Holding a Trucking Company Together Until an Heir Grows Up

The situation

What kept Kaveh awake was not the paperwork, it was the trucks. Twenty-two of them, a maintenance schedule that did not pause for grief, drivers who needed dispatch decisions made every single morning, and a fourteen-year-old at home who was, on paper, the eventual owner of all of it. If the company stumbled while everyone waited for that child to grow up, there would be no company left to inherit, no matter how carefully the will had been written.

Kaveh's brother had built the Hamilton trucking company over two decades and died suddenly, leaving a will that put the company's shares into a testamentary trust for his teenage daughter, to be held until she turned an age the will specified as old enough to take on real ownership. Until then, the trust named two trustees to manage the shares and the company's affairs on her behalf: Kaveh, who also became her caregiver and guardian, and Azadeh, the girl's mother and the deceased's widow, who had her own relationship with the business from years of handling its books.

The company itself was solid but not simple. Andriy, a longtime friend of Kaveh's brother, held a minority stake he had bought into years earlier when the business needed capital to expand, and he had always run daily dispatch operations alongside the deceased. With the deceased gone, Andriy was suddenly doing that work with no ownership say in anything beyond his existing minority position, and no clear line of authority above him besides two trustees, one of whom had never run a trucking business before and the other of whom was managing her own grief along with a teenager's.

The estate, including the company's value, the trust's other assets, and some real property, sat somewhere between three hundred thousand and six hundred thousand dollars in total, a meaningful sum built almost entirely on a business that needed someone making decisions every day, not once a quarter at a trustee meeting. Kaveh, a forklift operator by trade with no background in running a trucking company, understood immediately that the structure the will had set up was going to be tested quickly, and that the person it would test hardest was a fourteen-year-old who had just lost her father and had no say yet in how any of it was run.

Kaveh's first instinct was to simply keep the trucks moving and sort out the legal structure later, but a business this size does not run on instinct alone. Fuel contracts needed renewing, two drivers were asking about raises, and one truck had failed an inspection that needed roughly fifteen thousand dollars in repairs authorized within the week. Every one of those decisions, under the trust as written, technically needed both trustees to agree.

What the documents showed

The will and trust document, read closely, gave Kaveh and Azadeh joint authority over the company shares, with decisions requiring both trustees to agree. That structure makes sense on paper as a safeguard against one trustee acting alone against a beneficiary's interests, but it assumes both trustees are consistently available to weigh in. The document did not address what should happen if one of them could not participate for an extended period, an omission that is common in wills drafted without anticipating that a trustee, not just the testator, might become unable to act.

The trust also said little about Andriy's operational role beyond confirming his existing minority shareholding. He had no formal management authority under the trust, even though he was, in practice, the only person with the experience to run the company's day-to-day dispatch and maintenance decisions. The documents left a gap between who held legal authority over the shares and who actually understood how to keep the trucks moving, and that gap widened considerably once Azadeh's health became a factor.

Roughly four months into administering the estate, Azadeh was diagnosed with a serious illness that required extended treatment and left her unable to engage meaningfully with company decisions for long stretches. Every decision that legally required both trustees' agreement now risked stalling indefinitely, at exactly the point where the company needed timely calls on fuel contracts, driver retention, and a maintenance backlog on several of the older trucks. Kaveh could not act alone under the trust as written, and Andriy, watching decisions stall, began pushing hard for a buyout that would let him take a controlling stake and run the company without needing sign-off from a trust structure that had effectively frozen.

The documents made clear that the will's authors had planned carefully for the heir's eventual control, specifying an age and a clear path to full ownership, but had not planned at all for a co-trustee becoming unable to act in the meantime. That gap, not any ambiguity about who was meant to inherit, was what put the company at risk. The will's drafting had focused, understandably, on protecting the daughter from losing the business outright, without anticipating that the very mechanism meant to protect her could seize up entirely if either trustee's circumstances changed.

Reviewing the trust also surfaced a second issue: nothing in the document gave the trustees explicit authority to hire outside management or delegate operational decisions, even temporarily. Everything, as drafted, ran through the two named trustees personally, which meant that even a straightforward solution like bringing in someone experienced to handle day-to-day dispatch was not clearly available without the court's involvement first.

What we did

1. Reviewed the trust document for any mechanism to address a trustee's incapacity. We confirmed there was none, which meant Kaveh could not simply start acting alone under the existing terms no matter how urgent the company's daily decisions became, and that a court application would likely be needed to change how the trust operated before the operational backlog got worse.
2. Applied to court for direction on interim decision-making authority. Ontario law allows a trustee to seek the court's guidance when a trust's terms do not cover a situation that has arisen, and we asked for an order letting Kaveh make ordinary operational decisions alone while Azadeh's illness limited her participation, preserving her role for major decisions once she was able to engage.
3. Negotiated directly with Andriy rather than letting his buyout pressure escalate into a dispute. Andriy's frustration was legitimate even if his proposed solution was not, since he was carrying real operational weight with no formal authority, so we opened a conversation about what role and stake would actually reflect his contribution without displacing the heir's ultimate ownership.
4. Commissioned an independent valuation of the company. A neutral appraisal gave every party, including Andriy, a defensible number to negotiate around, and confirmed the company's value sat well within the estate's overall range, which kept the negotiation from being derailed by competing guesses about what the business was worth.
5. Proposed a partial sale of shares to Andriy rather than the full buyout he had first requested. Selling him a minority-to-near-equal stake from the trust's holdings, funded by his own capital rather than company debt, gave him meaningful ownership and a real say in decisions while leaving the trust with enough shares to guarantee the heir's eventual control.
6. Arranged for a professional operations manager to be hired. Bringing in someone with trucking industry experience to handle daily dispatch and maintenance decisions took the operational burden off both Kaveh and Andriy individually and reduced how much day-to-day authority the trust structure needed to delegate at all.
7. Built a revised trustee decision framework once Azadeh's treatment stabilized. We drafted an amendment, approved by the court, clarifying which decisions Kaveh could make alone during any future period where Azadeh could not participate, so the same bottleneck could not recur if her health required more treatment later.
8. Documented the heir's future path to full ownership under the new structure. The revised trust terms preserved the original age threshold and ownership path for the daughter, now layered on top of a company that had a working manager and a stable ownership structure rather than the fragile arrangement the original will had left behind.
9. Set up regular reporting so the daughter, as she got older, could follow how the company was being run. Even before she reached the age set for full ownership, we arranged for her to receive plain-language summaries of major decisions, so the transition to ownership would not be a sudden handover of a business she had never seen the inside of.

The outcome

The compromise cost something on every side, which is the honest measure of how it worked. The trust gave up a meaningful minority stake to Andriy, meaning the heir's eventual full ownership became a somewhat smaller slice of the company than the original will had contemplated, worth a real reduction measured in the tens of thousands of dollars against the company's total value. Andriy accepted a stake short of the outright control he had initially pushed for, and took on a fixed cost for the professional manager's salary that reduced his own returns as a shareholder going forward.

What the compromise bought in exchange was a company that kept running without interruption through Azadeh's treatment and recovery, drivers who were not left wondering whether the business would still exist in six months, and a decision-making structure that could survive the next health crisis without needing another court application. The professional manager brought operational stability that neither Kaveh nor Andriy, working alone under a stalled trust, could have provided consistently, and the maintenance backlog that had worried Kaveh most in the early weeks was cleared within the first few months under the new arrangement.

Azadeh's health stabilized enough over the following year that she resumed an active role as co-trustee, and the revised framework meant that when she later needed a further period of reduced involvement, the company's operations were not put at risk the way they had been the first time. Kaveh, for his part, stepped back from day-to-day involvement once the manager was in place, returning his attention to raising his niece rather than running a trucking company he had never trained for.

The heir remains on track for full ownership at the age the will specified, now inheriting a company with a working manager and a functioning shareholder structure rather than the version that nearly stalled in the months after her father's death. What she ultimately receives will be a smaller ownership share than the will originally described on paper, but a company that is still operating is worth considerably more than a larger share of one that had stopped making payroll decisions on time.

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