A buyer with no lawyer and a shareholder group that could not agree on timing

The situation

Sakura's first move was to skip the lawyers entirely. She sent Agus a personal email one Sunday evening, not a term sheet routed through counsel, laying out what she would pay for the clinic and software business he had spent twelve years building, and asking him to reply directly rather than involving advisors on either side until the broad strokes were settled. She was buying with her own accumulated wealth rather than through a fund with in-house counsel, and had decided, correctly or not, that lawyers on both sides would only slow the deal down.

Agus, a physiotherapist by training who spent his twenties treating patients before thinking about ownership, had co-founded the business with Dewi, a software developer who built the scheduling and records platform that eventually became as valuable, dollar for dollar, as the four physical clinics it served across Guelph. A third shareholder had joined years later with a smaller stake, drawn in during an expansion round when the company needed capital it lacked. By the time Sakura's email arrived, all three had developed different ideas about what came next. Agus, in his late fifties and increasingly tired of the administrative side of running clinics, wanted out completely and permanently. Dewi wanted to sell most of her stake but keep a meaningful piece and stay on to run the software side, the part of the business she still found genuinely interesting. The third shareholder wanted to sell only if the price cleared a specific number they had quietly settled on years earlier, and was otherwise entirely content to keep working as things were.

The business itself was healthy and growing, generating enough revenue and margin to put the deal somewhere in the thirty-to-fifty-million-dollar range, and Sakura's interest was genuine and well informed. But a sale that had to satisfy one shareholder who wanted a clean, complete exit, one who wanted a partial exit paired with a continuing role, and one who wanted a firm price floor or nothing, was never going to be a simple share purchase agreement, even before anything else complicated it further.

Then, three weeks into formal diligence, the clinic's operations manager flagged an active internal investigation into a complaint of workplace harassment involving a senior staff member, one that had begun quietly months earlier and was still ongoing. It had to be disclosed to the buyer as a matter of basic honesty and legal obligation. Nobody on the seller side particularly wanted to be the person explaining it to a buyer with no lawyer of her own standing beside her to help her process what the disclosure actually meant.

Why this was harder than it looked

On paper, this looked like two manageable problems sitting side by side: structure a sale around three shareholders' different exit preferences, and disclose an ongoing investigation properly and completely. In practice, each problem made the other significantly harder to manage, and Sakura's lack of her own counsel amplified both of them at once, in ways that were not obvious until we were already deep into the file.

Structuring the shareholder exits meant the purchase agreement could never simply be one price attached to one class of shares handed over cleanly. Agus needed a full cash exit with nothing left tying him to the business afterward. Dewi needed a rollover structure that let her reinvest a meaningful part of her proceeds into a continuing equity stake in the business under its new ownership, paired with a shareholders agreement governing her ongoing operating role and her own eventual second exit years down the road. The third shareholder needed the overall deal to clear a specific price floor or the entire structure had to be rebuilt to allow for a partial buyout of just the other two, leaving them as a minority holder in a business they no longer controlled. Every one of these pieces had to be negotiated as a single interlocking whole, because any change to Agus's terms immediately shifted what was left available for Dewi's rollover and for the third shareholder's floor calculation.

The investigation disclosure landed into that already delicate, carefully balanced structure at close to the worst possible moment in the negotiation. Normally, disclosing an active internal investigation to a buyer's counsel is a controlled, professional process: the facts are laid out plainly, both legal teams discuss how the situation affects representations, warranties, and indemnities in the agreement, and a price or holdback adjustment gets negotiated on a calm, procedural basis between people who do this regularly. With Sakura self-represented, there was no counterpart lawyer on the other side to have that conversation with at all. She read the disclosure herself, alone, reacted personally and emotionally rather than procedurally, and initially told Agus by email that she was walking away from the deal entirely, convinced the business must be hiding worse problems than the one actually in front of her.

We could not talk her out of that reaction the way we would with opposing counsel, because she had no shared professional framework to interpret what she had just read. We had to explain, in plain terms she could genuinely evaluate for herself without legal training, what an active workplace investigation does and does not typically mean for an incoming buyer, and what real protection a properly drafted indemnity actually provides against that kind of risk, all while being scrupulously careful never to cross the line into effectively advising her, since she was not our client and we could not appear, even inadvertently, to be managing both sides of the transaction.

What we did

1. Recommended Sakura get her own lawyer before anything else moved forward. We told Agus early, before any further substantive terms went back and forth, that continuing to negotiate directly with an unrepresented buyer on a deal this size created real risk for both sides of the table, including the risk that any agreement she later regretted could be challenged down the road as fundamentally unfair, and we declined to send her further substantive deal terms until she had retained counsel of her own.
2. Mapped the three shareholder positions before drafting a single document. We sat down with Agus, Dewi, and the third shareholder separately, in individual conversations rather than a group meeting where people tend to defer to each other, to understand what each of them actually needed to hear yes, then built a single structure, a mixed cash-and-rollover purchase with a price floor mechanism built in, that could satisfy all three without reopening the entire negotiation every time one person's terms shifted even slightly.
3. Managed the investigation disclosure as a formal, documented process. Once Sakura had retained counsel, we disclosed the investigation through a structured, written process, providing the facts known at the time, the concrete steps the clinic had already taken in response, and a realistic range of possible outcomes, rather than letting the information reach her informally and get filtered entirely through anxiety before her own lawyer ever had a chance to see it.
4. Negotiated an indemnity specific to the investigation's eventual outcome. Rather than offer a general representation that no such issues existed, which the disclosure had made impossible to give cleanly and honestly, we negotiated a specific indemnity covering costs arising from however the investigation ultimately resolved, with a holdback sized to a realistic, evidence-based range rather than either side's worst-case guess.
5. Rebuilt Dewi's rollover terms around the resulting price adjustment. Once the holdback reduced the total consideration available across the deal, we revisited the split between cash and rollover equity specifically for Dewi to make sure her ongoing stake still reflected a genuinely fair value, rather than letting the adjustment fall disproportionately on the one shareholder planning to stay involved in the business.
6. Held a joint call between both legal teams to reset the tone. After Sakura's lawyer came on board and reviewed everything, we proposed a joint call bringing both legal teams and all three shareholders together to walk through the revised structure openly, which did far more to rebuild basic trust between the parties than any further round of written exchanges could have accomplished.
7. Closed on a revised timeline the shareholders could actually plan around. The extra weeks needed for the investigation to reach a properly documented conclusion pushed the closing date back roughly two months from the original target, and rather than leave that delay open-ended and anxiety-inducing, we built it into a firm, revised timetable with checkpoints everyone on the seller side could plan their finances and expectations around.

The outcome

The sale closed with a price roughly eight percent below the figure first discussed between Agus and Sakura, reflecting the holdback tied to the investigation and the added cost of the extended timeline. Agus got the full, clean cash exit he had wanted from the beginning. Dewi kept a continuing stake and an operating role under the new ownership structure, on rollover terms adjusted fairly to reflect the revised overall price. The third shareholder's price floor was met, narrowly, only once the final structure was completely settled and signed.

The investigation itself concluded during the extended closing period, with corrective action taken against the staff member involved, a resolution that satisfied the conditions attached to the holdback and released most of the withheld funds back to the sellers within several months of the closing date. Sakura, once properly represented, went on to negotiate firmly but fairly through her own counsel, and the deal that eventually closed looked substantially more balanced and considered than the one she had first proposed by email, on her own, weeks earlier.

Nobody involved in this transaction would call it a clean, uncomplicated win. Agus and the third shareholder both accepted a lower price than they had originally hoped for, and Dewi's rollover value shrank along with everyone else's proceeds once the holdback was applied across the board. What the group avoided instead was something considerably worse: a buyer who walked away from the deal entirely over a disclosure she had misunderstood without help, or a closed deal that carried no real protection for a risk still genuinely unresolved at the signing table. Agus has since said the hardest part of the entire process was not the investigation itself but the six anxious days Sakura spent seriously considering walking away, before her own lawyer finally helped her see the structure clearly and negotiate her way back to the table.

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