Peter Freeman and Aaron Dressler of Halifax's Freeman Group (IG Private Wealth Management) put a number on the coming Atlantic Canada succession wave — and explain why the $2–5M subcontractor doing everything from the truck is the most exposed person in that wave.
Most contractors think about retirement the wrong way. They picture a date: the day the last invoice goes out, the tools go to the shelf, the phone stops ringing. What they don't picture is the three to five years before that date — the window when the decisions that actually determine what they walk away with either get made or don't get made. By the time the date arrives, it's too late to restructure.
Peter Freeman and Aaron Dressler have had that conversation with hundreds of business owners across Nova Scotia and Atlantic Canada, from Dartmouth to Liverpool to wherever the work takes them. Their practice, Freeman Group, operates under the IG Private Wealth Management banner and specialises in the intersection most advisors don't staff properly: what happens to a business and a family when the owner decides, or is forced, to stop.
Host Daniel Arsenault brought them on in Episode 66 of the Atlantic Construction Podcast as the show's financial-services partner. What followed was an 83-minute conversation that covered the mechanics — dividends versus salary, key-person insurance, bookkeeper versus accountant versus advisor — but kept returning to a harder truth: the financial disorder most owners carry quietly drains their capacity. The stress of unresolved planning costs productivity that never shows up on any line of the income statement.
The wave is bigger than most owners realize
Start with the scale of what's coming. Advisors across the industry estimate that something like 60 to 70% of Canadian small businesses will go through some form of succession or close within the next decade. Construction is over-exposed inside that number, for a reason that's visible on any job site: the workforce is aging at the same time the labour shortage is making it harder to find people who could take over.
For the contractor who built the business over twenty or thirty years, this is the core problem. "their retirement is locked up in that business and it's a scary time", as Dressler describes the situation his clients face. The business isn't just the asset — it's often the entire retirement. There's no pension, no RRSP large enough to substitute. Everything depends on whether the business sells, sells for the right number, and whether what comes out gets structured properly.
The planning horizon matters more than most people act on. Three to five years is not a luxury — it's the minimum runway to make the decisions that change the outcome. "three to five years before you even sell the business you should be doing a hard look with a professional", Freeman says. That's not a long time against a thirty-year career, but almost nobody starts it early enough.
Your accountant does not give you tax advice
One of the most practically useful parts of the conversation is the breakdown of what each professional in an owner's life actually does — and, critically, what they don't do.
A year-end accountant prepares and files. That's the job. The statement Freeman makes plainly is that "your accountant doesn't give tax advice and they don't charge you for it" — meaning the proactive modelling of how to structure dividends versus salary, when to trigger a capital gains election, how to use a holding company in a succession — that work belongs somewhere else. Most owners assume their accountant handles it. Many accountants let them assume that.
The advisors describe their own role as the financial quarterback: coordinating the bookkeeper, the accountant, and the lawyer, making sure the business side and the personal side are planned together. That last part matters because the two can't be separated. "I can't think of situations where it's only the business and not the personal side", Freeman says. The dividend the owner draws is taxable income to the family. The sale of the company triggers personal capital gains. Planning one without the other produces strategies that look clean in isolation and create surprises at closing.
For the owner who thinks they don't have time for this, the counterargument is blunt: "really the answer you're too busy not to to do it". The hidden cost of financial disorder isn't in the planning time — it's in the mental load an unresolved situation puts on someone who's also supposed to be running a business. Dressler frames it directly: owners who defer this work end up "30% less productive" over the years they keep putting it off. That's not a metaphor. It's a real drag on the actual business.
Know what you're actually protecting
Beyond succession, the conversation turns to what happens to the business if something happens to the owner first — or to a key member of the management team.
"how do I protect my management team I want to make sure they're stable" is the question Freeman says owners should be asking. If the person running operations, or the estimator who knows every relationship in the region, gets sick or dies, can the business survive long enough to find a replacement? Key-person insurance funds that gap. It's not complicated to structure, but it requires someone to have the conversation before the need arises.
The same logic applies to wills, and the advisors close on this with the kind of directness that comes from having walked grieving families through what happens when there isn't one. The statistic is roughly half of Canadian adults have no will. The point Freeman makes is that the absence of a will isn't the absence of one — it just means someone else wrote it. As he puts it: everyone has a will, it's just that without yours, Nova Scotia wrote it for you. The province's intestacy rules decide who gets what, and the province's priorities are not your priorities.
Having a will isn't quite enough, either. The follow-through question is just as important: "do you have a will yes does your executive know where it is". The executor who can't find the document can't act on it. This is the kind of detail that disappears in the gap between getting the thing done and actually completing the job.
The $750,000 that almost didn't exist
The most affecting part of the episode is a story Freeman tells about a year in which eight of his clients died. Eight in one year. He describes walking the surviving families through next steps, reviewing documents, locating policies.
One of those reviews uncovered something the family didn't know was there: a policy that hadn't been cancelled, hadn't been consolidated, had just been sitting. "the heartest day of my life was handing the $750,000 check to his wife", he says. The money existed because someone — in this case, their advisor — was in the habit of doing a complete review rather than assuming everything had already been found.
The practical lesson is not about grief. It's about the second set of eyes. Insurance policies accumulate over a career and businesses: key-person policies from past structures, group plans from previous employment, individual coverage taken out and then forgotten. A review finds them. Not reviewing means some of them stay lost.
Pick advisors who show up where you work
The episode also makes a case for how to evaluate the professional relationships you build, and it's straightforward: choose the people who come to you. "how can we really understand you if we haven't put safety glasses on", Freeman says, describing the practice of visiting client workplaces. An advisor who has stood in a warehouse and watched the operation understands something about that business that no financial statement conveys — the seasonal cash flow, the risk concentration, the physical reality of what has to keep functioning when the owner exits.
Referrals, they note, compound when clients feel good about decisions. "you always make me feel good about the decisions I've made" is what Freeman says he hears from the clients who refer others. That isn't a sales line — it's a description of what good advisory actually produces: confidence in the decisions that have already been made, not just the ones ahead.
The show's audience skews toward the $2–5M subcontractor doing millions in revenue, still running lean, still invoicing from the truck. That's exactly the owner this conversation is for — old enough that exit is coming into view, busy enough to have deferred every conversation about it, and the kind of person who figures they'll sort it out when the time comes. The time-to-sort-it-out is three to five years before the time comes.
Freeman Group Private Wealth Management (freemangroup.ca) is a Halifax-based practice operating under IG Wealth Management, advising business owners and high-net-worth families across Atlantic Canada on retirement, estate, tax, insurance, and business succession planning. A first conversation is a free hour.
Guests: Peter Freeman CFP and Aaron Dressler CFP, Freeman Group Private Wealth Management. Featured on Episode 66 of the Atlantic Construction Podcast. Watch the full episode. Also featured: IG Wealth Management, Trinity Energy Group, Payzant Building Products, and Luminous Labs. Succession planning horizon (3–5 years pre-exit): CFIB research.