Peter Freeman and Aaron Dressler of Freeman Group Private Wealth Management sat down with the Atlantic Construction Podcast to work through a question most owners avoid: if you didn't come back tomorrow, would the business keep running — or collapse? The answer tells you everything about what your company is actually worth.
Most construction owners think succession is something they'll deal with later. Peter Freeman, a CFP and founding advisor at Freeman Group Private Wealth Management — a Halifax practice operating under the IG Wealth Management network — has been watching that instinct cost people for nearly three decades. He joined co-advisor Aaron Dressler on Episode 74 of the Atlantic Construction Podcast, and within minutes the conversation landed on a litmus test that has no comfortable answer.
"if you were to die today or not come back to work for whatever reason how would the business evolve" — that was Freeman's question. Not as a scare tactic — as a diagnostic. The construction owner who can vanish for a month and find the business better when they return has built something sellable. The one who is the business has built something that ends when they do.
Freeman runs the same test on his own practice. His answer: Aaron Dressler could step in. That's the whole point. The more you build a team that doesn't need you in the office, the more you've built an asset rather than a job.
The trillion-dollar transfer that's already happening
This is not a theoretical problem. According to the Canadian Federation of Independent Business, more than 50% of business owners will change hands in the next 10 years. Freeman put the scale plainly: trillions of dollars in business value are moving between generations across the country, and Atlantic Canada is right in the current. Many of those businesses will not survive the transfer — not because there are no buyers, but because the owners never had a real plan.
The timing problem isn't abstract either. "more than 50% of business owners will change hands in the next 10 years" — Freeman put it plainly — but people get sick, have accidents, and die on schedules they don't control. The owner who plans to think about succession at 65 may not get the chance.
Freeman had already seen what preparation looks like before the pressure hits. His practice had digitized its records years before COVID forced the issue on everyone else, which meant when lockdowns landed, they were the ones who could keep working without scrambling.
Who actually buys your business — and why it's probably not your kids
The biggest assumption construction owners make is that the business will pass to the next generation. Freeman and Dressler see it break down constantly. "the intention is there hey I want to pass this on to my kids but often the kids don't want to do it" — Freeman hears this constantly. A child in their 40s or 50s has their own career, their own family, their own direction. They were never asked.
So who are the real buyers? Often, the people already running things. If the management team already keeps the business functional when the owner is gone — and the best owners are the ones who are on the floor with their people rather than behind a desk — then that team is the natural exit. "can you create some structure to allow your management team to buy you out because then the business is functioning" — that's the question Freeman asks first. A management buyout keeps the operation intact, the relationships in place, and the knowledge in the building.
A less obvious candidate is a key client or major subcontractor. If one company represents a disproportionate share of your revenue, Freeman's question is whether it makes more sense to sell to them than to watch the relationship collapse when you retire. "shouldn't we be talking to that company about them buying you out because if your business just closes up" — he asked — and if the business closes, the client loses a supplier they depend on. That's alignment worth a conversation.
The hardest case is the sole operator: the one-person service business that lives and dies with the owner. Most owners in that position stay past 65 without a plan. "this is you know a sole business that it's a service related business it's going to live and die with him" — Freeman puts it honestly. That business doesn't get sold — it gets wound down. Better to plan for that honestly than to hope otherwise.
The tax tools most owners underuse
Once the succession frame is set, the conversation turned to the tax side — and there is a long list of tools construction owners rarely use fully.
RSPs. The common guilt about unused RSP room is misplaced. If you sell a business and have a large capital gain you can't shelter, accumulated RSP room can be the tool that absorbs it. "if they sell their business and they have a huge capital gain that they can't shelter then it comes in huge value" — that's the scenario where banked RSP room earns its keep. Don't panic about unused room; it may be waiting to do exactly that job.
Individual Pension Plans. Business owners without an employer pension have access to an IPP — a structure that lets them deduct more than a standard RSP allows. "you can deduct more money deduct more income you can have a larger deduction than you could for an RSP" — Freeman's summary of the IPP advantage. It requires a corporate structure but is straightforward to set up with the right advisor.
Salary and dividends. Most incorporated owners pull income as dividends only, because dividends are taxed at a lower rate. The smarter approach mixes them. "they will pull money out as salary because they do want to create some taxable income that creates RSP room" — the mixed approach. Salary also builds CPP contributions; dividends preserve the preferential rate. The right split depends on your situation and changes as the business grows.
Wealth insurance. Corporate-owned life insurance can be set up as a deductible business expense and is, in Freeman's view, the largest legal tax shelter available in Canada. "the biggest tax shelter that really is out there in this country is life insurance" — his words. The corporate ownership structure changes the economics significantly compared to an individual policy.
TFSAs. The TFSA is widely misunderstood as a savings account. Freeman's framing is more useful: "think of the tfsa as just a box Inside the Box you could put many different things often the default is cash" Put growth investments in it, not cash at near-zero interest. A TFSA can also be used to pass money privately to one child without disrupting an estate's balance among siblings.
The trust reporting trap most owners walked into
One recent regulatory change blindsided many clients. Under CRA rules introduced in 2023 (later deferred a year), joint ownership of a child's home or a parent's bank account now constitutes a trust that must be reported. Most people have no idea they're in one.
Freeman described a client conversation: "did you become a joint owner in her bank account oh yes... I said do you know you're in a trust relationship" They didn't. This is exactly the kind of rule that changes quietly while an owner is focused on running a business — and missing it has real consequences. Keeping up with it is the advisor's job, not the owner's.
Build the financial team — you're not supposed to know this alone
The throughline across the whole conversation is permission to not know everything. "I wouldn't expect you to know everything about financial planning" — Freeman said. A construction owner is not expected to master tax law the way a planner is not expected to know how to frame a wall. What matters is having the right team around you.
Freeman describes the planner's role as "so we're the financial quarterbacks" — convening the accountant, the banker, and the lawyer so they're working from one agreed plan rather than silos that don't talk to each other. Most owners who have all three of those professionals still don't have them coordinated. That coordination is what a financial planner actually provides.
The banks are not filling that gap. "their role is into education clients it's often just to sell a product and move on" — Freeman noted. A branch manager has sales targets; an independent planner's interest is aligned with the client's. Understanding that distinction is worth the conversation.
Programs you may be missing right now
A few specific programs came up that clients consistently miss:
The First Home Savings Account is a newer program with strong mechanics: "the kids can put up to $8,000 a year in it's tax deductible like you would be putting money to an RSP" — and the withdrawal for a first home is tax-free on the other end. It's an RSP and TFSA combined for one purpose. If you have adult children saving for a home, this should be on your radar.
The RDSP — Registered Disability Savings Plan — provides government matching for families with a disabled child or grandchild. "here's a program where the government's giving thousands of dollars a year of free money" is how Freeman put it. Families miss it because the disability approval process feels like a hurdle; it's worth clearing.
Finally, beneficiary designations. Most owners name their will as the instrument for distributing RSPs, TFSAs, and life insurance. That's usually wrong. "none of those things should be named in your will in a lot of situations" — naming beneficiaries directly by percentage on those instruments bypasses probate entirely, speeds the distribution, and reduces legal cost. A 28-year-old will with the original company structure on it is almost certainly out of date anyway. "it always amazes me how few people have current Wills in place" — Freeman said.
Start with the question, not the paperwork
The guest pitch at the end of the episode is the right note to close on. There is no charge for an initial conversation. The advisors at Freeman Group work with owners who aren't sure whether they have a real succession plan — and that uncertainty, rather than a completed plan, is the right moment to start.
If a vacation or an unexpected diagnosis would leave the business in chaos, that's the answer to the test. The time to do something about it is before the test becomes real.
Guests: Peter Freeman, CFP and Aaron Dressler, CFP — Freeman Group Private Wealth Management, a Halifax practice operating under IG Wealth Management. Featured on Episode 74 of the Atlantic Construction Podcast. Watch the full episode. Receipt sources: CFIB — over $2 trillion in business assets changing hands; CRA — First Home Savings Account contributions; CRA — trust reporting rules for bare trusts.