Significant liquidity events can feel like winning the lottery. Only the stakes are much higher, given the fruits of your hard labour could be worth $20 million or even $100 million-plus. For many, liquidity events require radical shifts in mindset and strategy, says Thane Stenner, founder of Stenner Wealth Partners+ at CG Wealth Management, Chairman Emeritus of ultra-high-net worth network Tiger 21 in Canada, and previously held award-winning consulting roles at Morgan Stanley/Graystone Consulting based in California as Managing Director, International Client Advisor, Institutional Consulting Director, Alternative Investments Director and Portfolio Manager.
He is an expert advisor to a select group of ultra-high-net-worth clients from across Canada, with net worths between $25 million and $3 billion. “Some have had multiple liquidity events,” says Stenner, whose virtual/in-person Multi-Family Office/Outsourced CIO Consulting team deals with 51 clients across Canada including many Single-Family Offices (SFOs) (previously #1 Ranked California based consulting team on the Barron’s Top Institutional Consultants 2020 List, and now based back in Canada for the last four years). Thane and his US and Canadian teams have guided/transacted on billions of dollars’ worth of securities over his career. CG Wealth Management currently advises on C$120.4 billion in client assets globally.
Warren Buffett once said: ‘An idiot with a plan can beat a genius without a plan.’
Plan for the unexpected, and for anticipated deals, too
This isn’t to imply families facing a liquidity event are prone to foolishness. They’re anything but. Yet it underscores the importance of advanced planning with liquidity events. “Offers to purchase can sometimes come with very little notice,” Stenner says.
“Hence, planning should be ongoing and done early and often so you have confidence to make decisions whether you’re going through a planned selling process or an offer comes unexpectedly.”
Planning for a liquidity event is best done at least a year in advance. But the earlier the better, says Toronto lawyer Julian Franch, specializing in tax and trusts for private clients at Cassels. “You need enough time to implement presale tax optimization planning and then to have even more time so the business can grow to really take advantage of that plan.”
The right structure matters
One reason time is beneficial is owners can work with experts like Stenner, Franch, and his colleague Samantha Prasad, also a lawyer at Cassels specializing in helping private clients deal with liquidity events. “We help develop the right corporate and personal tax structures to help, when clients sell, maximize value and limit the necessary tax they pay,” she notes.
Among the advice Franch and Prasad might suggest is making more adult family members shareholding owners a few years in advance of going to market. This way, the business can continue to grow in value, allowing each owner to fully benefit from their individual lifetime capital gains exemption of $1.25 million, worth about $334,000 in tax savings per investor/owner. “But if you don’t do any planning to set that up, you might end up the lone shareholder, paying more tax than necessary.”
Appreciate the art of deal-making
No one deal looks like the other, but they all follow a few frameworks. Deals can be all-cash from private equity, for example, or an exchange (via Section 85) of equity from the purchasing company—among others. Not all deals may be what they seem at first glance. Even those offering the highest cash value may not be the best choice, Stenner says. “An all-shares transaction deal, for instance, may be better than the slightly higher one in all cash.” Of course, it’s hard to know unless you’ve pre-planned and can then model various scenarios around the offers, guided by an advisory team of money managers, tax and estate planners and, of course, a mergers and acquisitions expert. “A lot of deals fall apart because the owner has anxiety over best choice, but we can build scenarios to help them decide with confidence,” Stenner adds.
It’s a done deal, so now what?
Sealing the deal is really just the start. Now, comes figuring out how to manage the liquid proceeds to your best outcomes. Stenner’s first advice here is simple: take a pause. “A lot of entrepreneurs want to put the money to work right away.”
Instead, “pump the brakes” and ask yourself if you would have paid that much for your business? Stenner frequently does this mental exercise with clients, and their answer is almost always, ‘No, I received more than I thought I was going to!’ Then he reminds them to be mindful not to do the same with the business sale proceeds, i.e., potentially ‘buying back high’ into the public markets after ‘selling high’.
“If they sold their business for a high price, public markets are likely trading higher too, which for an investor with a lot of capital to deploy is a big risk.” There is a strong correlation here. When business owners are offered premium prices to sell, it tends to be when public markets are also expensive.
You need time to properly plan and develop a written Investment Policy Statement (IPS) setting out how to deploy capital over the next 12 to 24 months. “It’s like a blueprint for a new home.” If you “sell high”, you have to be careful not to rush and ‘buy high” into the public markets. A proper deployment plan should be developed.
Stenner adds an abundance of caution is always welcome because the larger the sum invested, the bigger the bruise a bear market can make. “Invest too aggressively in a hot market that then declines 20 per cent initially, and that initial $10-million paper loss (on a $50-million net of taxes business sale, for example), stings so much more.”
Change your money mindset
Large liquidity events are often emotionally challenging because they can involve so much change. “Up until that point, most owners are effectively asset rich, cash poor,” Prasad notes. “So, it’s a dramatic change.” One big challenge for individuals is taking “their hands off the wheel” via delegation to wealth managers, Stenner adds, no small feat for entrepreneurs used to being in full control.
Yet they must give up the reins somewhat, and an experienced advisory team makes it easier. Stenner notes his team generally reaches out to clients after a liquidity event as much as 25-50 times the first year to smooth out the transition and help the newly liquid former business owner gain full confidence in their new financial state and wealth management game plan.
“We want them to be 100% comfortable as chairperson of their liquid capital.”
A public view on private wealth
Big business deals often don’t go unnoticed. They can be big news. “Suddenly, all your new, best friends and family come knocking.” Stenner says you want a discreet wealth management team that can be a “privacy moat” to protect yourself from a deluge of ‘invest in my business’ requests.
It’s not just the parents needing help; it’s the children too. “You’d be shocked how news gets to the kids at school.” Stenner further notes having many conversations with entrepreneurs’ children, helping them understand and navigate newly liquid wealth. “This is a soft point area that can see a lot of problems if you don’t address it early on and proactively.”
Build a team of expert advisors
No one advisor can handle the entirety of a liquidity event. It takes a veteran team. “You want to ensure your group of advisors have a lot of experience in this area,” Stenner says. But not many do, which means turning to third-party experts. Even Stenner’s extensive in-house team needs to turn to third-party experts like Prasad and Franch for legal and tax strategies, as well as working collaboratively with clients’ accountants.
“Collaboration is essential,” Franch adds. Of course, an experienced quarterback—like Stenner—is needed to coordinate all moving parts. “The bottom line is you need specialists,” Stenner adds. “Because a lot of times you’ve been so focused on building your business, you’ve likely never given these new challenges much thought.”
*Responses have been lightly edited for clarity and length.
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Thane Stenner Interviews/Articles, Member of Canadian Family Offices.
About Stenner Wealth Partners+
Stenner Wealth Partners+ (SWP+) is an in person/virtual Multi-Family Office/Outsourced CIO Consulting team of financial/wealth specialists with a boutique approach and global perspective. SWP+ serves Canadian and US investors/households with generally a minimum of 10M+ in investable assets or 25M+ net worth. As a CG Wealth Management team, SWP+ is a highly exclusive practice team with one of Canada’s largest independent wealth management firms. Client Range of Net Worths: between $25M To $3B+. New Client Engagements: Strategically on-boards only 6-8 new key relationships annually.
About CG Wealth Management
The global wealth management business is entrusted with C$120.4 billion in client assets.1 The wealth management operations of the Canaccord Genuity Group (CG Wealth Management) provide comprehensive wealth management solutions and brokerage services to individual investors, private clients, family offices, Donor Advised Funds (DAFs), and intermediaries through a full suite of services tailored to the needs of each client.
1Canaccord Genuity Annual Report, March 31, 2025
Disclaimer: This story was created by Canadian Family Offices’ commercial content division on behalf of Stenner Wealth Partners+ at CG Wealth Management, which is a member and content provider of this publication. CG Wealth Management is a division of Canaccord Genuity Corp., member of CIPF and CIRO. Thane Stenner’s views, including any recommendations, expressed in this article are his own only, and are not necessarily those of Canaccord Genuity Corp.