Plain-language commentary on developments in Canadian business, technology, and regulatory law — written for US companies, in-house counsel, and US law firms working across the border.
AI is the ultimate pleaser: ask for X and you get X. A good lawyer takes the time to see that what you actually need is Y — the discernment and judgment you can’t automate.
Read More →Because the exemption is per person, a family trust can multiply it across several beneficiaries on a business sale — how it works, and why the second-trust value step-up runs into GAAR and the surplus-stripping rules.
Read More →Canada taxes you as if you sold everything the day you die, so a growing company means a growing tax bill. An estate freeze caps it at today’s value — what it is, and the moments to consider one.
Read More →Plain-language definitions of the Canadian business law terms owners meet when they buy, sell, or pass on a company — earn-outs, shotgun clauses, the oppression remedy, estate freezes, EOTs, and the LCGE.
Open the glossary →You and your partner have hit a wall. Before it becomes a lawsuit, the ladder from honest negotiation to mediation to a buyout — and how a lawyer and mediator can help you settle.
Read More →A neutral helps you settle a business dispute privately, often in a day, for a fraction of litigation. How commercial mediation works step by step, what it costs, and when it beats court.
Read More →Who decides, what it costs, how long it takes, and what each gives you. When mediation beats a lawsuit for a business dispute — and the cases where litigation is the right tool.
Read More →Sell to a third party, transfer to family, a management buyout, an Employee Ownership Trust, or wind down. The five succession routes compared — tax, timing, control, and legacy.
Read More →The hardest handover. Separating management, ownership and fairness, the estate freeze and family trust, the 2024 intergenerational transfer rules, and being fair to kids not in the business.
Read More →Take money off the table or bring in a partner without selling the whole company. Selling existing shares vs issuing new shares, valuing a minority stake, the shareholder agreement, and keeping control.
Read More →Your buyer can’t pay all at once? Staged buy-ins, vendor take-backs, and earn-outs — the security and terms that protect you until you’re paid, plus the capital gains reserve.
Read More →Own private-company shares? A single will can cost your estate thousands in Ontario probate tax. How dual (primary + secondary) wills keep your company out of probate — confirmed valid in Milne Estate.
Read More →A growing company means a growing tax bill at death. An estate freeze caps it at today’s value and passes future growth to the next generation, tax-deferred. How it works, and the catches.
Read More →A will only matters when you die. If you’re alive but can’t run the company, who signs? Ontario powers of attorney for business owners, coordinated with your shareholder agreement.
Read More →Hiring in Canada or signing Canadian customers? When a U.S. company needs a Canadian subsidiary, federal vs Ontario incorporation, director-residency rules, GST/HST and payroll — and what goes wrong.
Read More →Fifty-fifty and frozen? How to break a shareholder deadlock without litigation — shotgun clauses, buyouts, mediation and arbitration, with court remedies as last-resort leverage.
Read More →Yes — a contract is not void because AI wrote it. The real risks are U.S. law bleeding in, clauses that are unenforceable in Canada, missing terms, and the occasional invented citation.
Read More →Family firms drive nearly half of Canada’s private-sector GDP, and most die before the third generation. What kills them is rarely the business — it’s the family. The governance structures that work, and the ones that quietly fail.
Read More →You invested in a private company, get no dividends, and never signed a shareholder agreement. It feels airtight. It isn’t — a working lawyer walks through your real options, including the one most people have never heard of.
Read More →Harvey just raised at an $11B valuation and most big firms already use it. A working lawyer’s read on what AI actually changes for clients and lawyers — and what it can’t.
Read More →One owner? You don't. Two or more? You do — and specific moments (a new partner, an investor, a family business, giving an employee equity, a 50/50 split) turn it from 'should' into urgent.
Read More →The issuer's side of a private raise: the NI 45-106 exemption, verifying each investor, the subscription documents, the 45-106F1 filing, and the mistakes that blow the exemption.
Read More →Who qualifies as an accredited investor in Canada under NI 45-106, how you actually become one, why the status unlocks the private exempt market — and the risks that come with it.
Read More →The real trade-offs between incorporating and a sole proprietorship in Canada — personal liability, tax deferral, the lifetime capital gains exemption, cost, and when incorporating pays off.
Read More →Mixing family and business without governance is how good companies tear themselves apart. The structures — shareholder agreement, board, roles, succession — that keep a family business intact.
Read More →AI can cut your legal spend on first drafts, plain-language explanations, and prep — but not on judgment. Which models to use, the confidentiality and accuracy risks, and the AI-plus-lawyer division of labour.
Read More →The hardest talks between business partners get put off until they explode. Why they get avoided, how to raise them early and well, and the agreement that turns fights into looking up the answer.
Read More →Keep going, renegotiate, or get out? A framework for reading a partnership, deal, or dispute — when to hold, when to fold, when to walk away, when to run — and building clean exits in advance.
Read More →If your business has more than one owner and no shareholder agreement, the law writes one for you — and you won't like it. Decision-making, transfer restrictions, buy-sell and shotgun clauses, and why to sign while everyone still gets along.
Read More →Due diligence is the buyer's deep inspection of your business — corporate records, contracts, IP, financials, liabilities. What they check, how findings quietly reprice a deal, and how to be ready before you go to market.
Read More →Selling to an employee ownership trust can shelter up to $10 million of your capital gain from tax — now permanently, after Ottawa dropped the 2026 sunset. What an EOT is, who qualifies, and the 10-year clawback to watch.
Read More →Paste a contract into a public AI tool and you may be breaching an NDA, waiving confidentiality, and weakening privilege — without a single thing going wrong. What to check before you do it.
Read More →An earn-out pays part of the price later, based on performance in a business the buyer now controls. Choosing the metric, protecting the runway, and the employment overlap that can cost you the money.
Read More →The LOI looks preliminary, but it's where price, structure, and exclusivity get anchored. Which clauses actually bind, what to leave open, and why to get advice before you sign.
Read More →Ontario banned most employee non-competes in 2021 — but in a business sale they still bind. When a non-compete holds up in Canada, and the reasonableness test that decides.
Read More →Tariffs make a deal more expensive, not impossible — so force majeure rarely saves you. The delivery terms, duty allocation, and tariff clauses that actually decide who absorbs the cost in Canada–US supply deals.
Read More →As extreme weather becomes foreseeable, boilerplate force majeure quietly stops protecting you. Where climate risk shows up in your supply contracts, leases, insurance, and diligence.
Read More →Business value is earnings times a multiple, and the multiple is about risk. The changes that raise it — owner-independence, recurring revenue, clean legal diligence — and why they have to start a year or two before you list.
Read More →Sellers usually want a share sale, buyers usually want an asset sale, and the difference can change your after-tax proceeds dramatically. The lifetime capital gains exemption, employees, and the section 84.1 trap for family and employee deals.
Read More →There's no law that says you must hire one. What the lawyer actually does in a business sale — the representations, the tax structure, the closing — and what tends to happen without one.
Read More →A practical guide for US software companies, in-house counsel, and operators whose product, customers, or employees touch Canada. PIPEDA, Quebec Law 25, BC PIPA, and where US privacy programs typically fall short.
Read More →What US companies need to know about hiring their first Canadian employee — reasonable notice, worker classification, equity grants, restrictive covenants, and the permanent-establishment trap.
Read More →What US drafters most often miss when their limitation-of-liability and exclusion clauses are tested in a Canadian court. A practical look at the post-Tercon framework and what it means for commercial contracts.
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