Treadstone Associates
Case File · Securities Law

Rollover shares issued without confirming a prospectus exemption

Anonymised, illustrative composite. Part of the purchase price for an Ontario building-materials distributor was paid in shares of the buyer's own acquisition vehicle. Issuing them to eleven people was a distribution of securities, and nobody had confirmed an exemption covered all eleven.

Treadstone Associates · Updated 2026

At a glance

  • • Ontario share purchase of a building-materials distributor for $18,000,000; $3,400,000 of the price was paid in shares of the buyer's newly formed acquisition vehicle, issued directly to eleven of the vendor's individual shareholders.
  • • Issuing a corporation's own treasury shares to a purchaser is a “distribution” under the Securities Act (Ontario), and no person may trade in a security that is a distribution unless a prospectus exemption applies.
  • • Five of the eleven recipients clearly fit an exemption in National Instrument 45-106. Six did not fit any category cleanly, and had to be re-tested individually.
  • • Of those six, four qualified as accredited investors on retesting. Two qualified under no exemption identified, and the deal proceeded with a voluntary report to the regulator for their allocations.
  • • Every recipient's shares, however issued, carried a resale restriction under National Instrument 45-102 that nobody had explained at closing.

The situation

A private equity-backed acquisition vehicle bought a building-materials distributor for $18,000,000. It was structured as a share purchase, and $3,400,000 of the price was satisfied by the acquisition vehicle issuing its own common shares directly to eleven individual sellers — family members and long-serving employees who had accumulated minority shareholdings in the target over the years — as rollover consideration for their target shares. Deal counsel focused on the section 85 rollover mechanics and the closing timetable. The issuance itself was treated internally as paperwork for a private transaction, and nobody confirmed that a prospectus exemption covered every recipient.

The problem

Issuing a corporation's own unissued shares to a purchaser is a distribution of securities. Distributing securities without a prospectus is prohibited unless an exemption applies. Of the eleven recipients, two became officers of the acquisition vehicle at closing and two more were their immediate family members — clear fits for the private issuer exemption's enumerated categories. Two more were existing security holders of the vehicle before the rollover closed, another clear fit. The remaining six were long-serving employees or minority shareholders of the target with no family, officer or director relationship to the acquisition vehicle or its sponsor, and none had the net financial assets or income to qualify as accredited investors on an initial review. None of the private issuer exemption's other enumerated categories fit them cleanly either.

The numbers

$18,000,000 total consideration; $3,400,000 paid in rollover shares to eleven recipients. Five fit an exemption on the first review. Of the remaining six, four qualified as accredited investors once retested against updated financial information; two qualified under no exemption identified. Securities counsel retained after closing to review the issuance billed roughly $85,000 to work through it.

The rule that decided it

The Securities Act (Ontario) defines “distribution”, where used in relation to trading in securities, to mean, among other things, “a trade in securities of an issuer that have not been previously issued” — exactly what happened when the acquisition vehicle issued its own new shares to the eleven sellers. Section 53(1) then provides that “no person or company shall trade in a security on his, her or its own account or on behalf of any other person or company if the trade would be a distribution of the security, unless a preliminary prospectus and a prospectus have been filed and receipts have been issued for them by the Director.” Absent a prospectus, an exemption has to cover the distribution.

National Instrument 45-106 supplies those exemptions. Section 2.4 defines a “private issuer” as an issuer “that is not a reporting issuer or an investment fund”, whose securities other than non-convertible debt “are subject to restrictions on transfer that are contained in the issuer's constating documents or security holders' agreements” and “are beneficially owned by not more than 50 persons, not including employees and former employees of the issuer or its affiliates”. The acquisition vehicle, with roughly fifteen holders total after closing, comfortably met that test. The private issuer exemption then allows a distribution only to purchasers in enumerated categories — directors, officers, founders and control persons; their close family; close personal friends and close business associates of those persons; existing security holders; accredited investors; and, as a residual category, “a person that is not the public”. Six of the eleven recipients did not fall cleanly into any named category, leaving only that residual, deliberately soft, catch-all to rely on — not a basis to issue shares without a considered legal opinion.

Read the unit. The obvious-sounding fallback — that a share-for-share rollover inside a private acquisition must qualify as a reorganization exemption — does not hold up on the text. Section 2.11's business combination and reorganization exemption applies to a distribution made under “an amalgamation, merger, reorganization or arrangement that is under a statutory procedure”, or one approved through an information circular process, or a dissolution or wind-up. A straight share purchase agreement, negotiated and signed without a statutory plan of arrangement or amalgamation, is none of those things, so section 2.11 was never available here regardless of how the deal was described internally.

The outcome

Securities counsel engaged after closing confirmed the acquisition vehicle qualified as a private issuer and that five of the eleven recipients fit an enumerated category without difficulty. Of the remaining six, four were re-tested against the accredited investor exemption in section 2.3 and qualified once updated net-financial-asset figures were obtained. Two qualified under no exemption identified. Unwinding was not realistic — the shares were issued and the target had already been amalgamated into the acquisition vehicle. The parties made a voluntary report to the regulator for those two allocations and negotiated a resolution rather than waiting to be found.

What it would have cost otherwise

A distribution made without an available exemption, left unaddressed, exposes the issuer to regulatory enforcement and can taint every subsequent distribution the issuer makes while the defect is unresolved — a live problem for a company just beginning to raise acquisition financing for its next deal. Confirming the exemption for all eleven recipients before closing, rather than after, would have cost a fraction of the $85,000 clean-up review and avoided the voluntary report altogether.

The tell

The tell was in how the rollover was described internally: as “paperwork” rather than as an issuance. Every recipient's information sheet for the deal quoted a rollover percentage and a share count. None of them mentioned that receiving those shares also meant receiving a resale restriction — the exemption used, wherever it applied, came with a seasoning period on resale under National Instrument 45-102, and nobody had explained that at closing either.

Takeaways

  • • Issuing an acquisition vehicle's own shares to sellers as rollover consideration is a distribution of securities under the Securities Act (Ontario), whatever the deal's overall shape looks like.
  • • The private issuer exemption's enumerated purchaser categories have to be checked one recipient at a time — a rollover group of family, employees and minority holders will not all fit the same category, and the residual “not the public” catch-all is not a substitute for that review.
  • • A statutory plan of arrangement or amalgamation can access the business combination and reorganization exemption; an ordinary share purchase agreement cannot, no matter how the deal is described.
  • • Confirm and disclose the resale restriction before closing — every exemption in this corner of National Instrument 45-106 comes with one, and it is not optional information for the people receiving the shares.

Sources

  • • Securities Act, R.S.O. 1990, c. S.5 — s.1(1) definition of “distribution”, paragraph (a); s.53(1), the prospectus requirement.
  • • National Instrument 45-106 Prospectus Exemptions — Ontario Securities Commission unofficial consolidation current to 2022-01-05 — s.2.3 (accredited investor), s.2.4 (private issuer, including the purchaser categories), and s.2.11 (business combination and reorganization, confirming it does not reach an ordinary share purchase agreement).
  • • No Treadstone Law page addresses prospectus exemptions or securities-law distribution rules; the library's franchise resale exemption content is a different regime (the Arthur Wishart Act) and is not on point, so no link is added.

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