The Advisors Your Parents Picked Aren't Necessarily Yours.
Aug 12 2026 — A new generation is stepping into positions of power across business, family, and community. The team they build around them will define what happens next.
READING TIME: 5 Minutes
PEEL REGION, ON - Something is shifting in the GTA's business and professional community. Quietly but unmistakably, a new generation is taking the reins.
In family businesses across Brampton, Mississauga, and Caledon — sons and daughters are being handed the keys to companies their parents spent decades building. In boardrooms and professional firms — younger partners are being elevated into leadership positions they've been preparing for without fully realizing it. In community organizations — a new generation of influencers is stepping into roles that carry real weight and real responsibility.
This is not a gradual transition. For many, it happens in a moment. A conversation. A handoff. A decision that changes everything about how they move through the world.
And with that moment comes a question that doesn't get asked out loud nearly enough.
Who is actually in my corner?
The Inherited Advisory Team
Most second generation professionals inherit more than the business. They inherit the relationships — the accountant who has been with the family for twenty years, the lawyer who drafted the original shareholders agreement, the insurance broker who has been renewing the same policies since before they graduated high school.
These advisors served their parents well. In many cases they did extraordinary work building the foundation that made the transition possible.
But the second generation's needs are different. The risks are different. The assets are different. The pace of decision-making is different. And the expectation of how an advisor communicates, responds, and engages is completely different.
The second generation grew up in a world of immediacy. They expect their advisors to move at the same speed they do. They don't want long explanations. They don't want to be educated like they're new to the room. They want clear, honest, direct counsel from people who treat them as the decision makers they already are.
What they often get instead is a version of the same energy their parents navigated for decades. Advisors who move slowly. Who over-explain. Who say this is what it is as if that closes the conversation. Who are unresponsive when something needs to move quickly.
The second generation notices. And increasingly — they are deciding to build their own team.
The Team You Build Is the Foundation You Stand On
The advisors you choose in the next two to five years will shape the trajectory of everything you're building.
This is not hyperbole. The right lawyer protects your agreements and your future. The right accountant structures your wealth efficiently. The right financial advisor positions your assets for growth. And the right insurance advisor — one who understands the complexity of what you have and what you're building — ensures that none of it is exposed at the moment it matters most.
These relationships compound. The advisor who understands your situation today understands it better in three years. They bring you opportunities, introductions, and intelligence that an advisor managing you at arm's length never could.
The wrong advisors cost you more than their fees. They cost you time, exposure, and the compounded value of a relationship that should have been built correctly from the start.
What the Right Advisor Looks Like
Early in my career as an underwriter, I received a call from a broker I had never met. She said — I don't even know what company you're with, but my boss told me to call you and said that you would help.
That was the greatest professional compliment I have ever received. It told me that the reputation I was building wasn't about my title or my firm. It was about whether people believed I would actually show up for them.
That call shaped everything about how I approach this work. And it's the standard I hold every advisor relationship to — including my own.
The right advisor for this moment in your life has these qualities:
They move at your pace. Responsive. Direct. No runaround. When something needs to happen they make it happen and they tell you where things stand without you having to ask twice.
They tell you the truth. Even when it's not what you want to hear. The advisors who tell you what you want to hear are the most expensive ones you'll ever have — you just don't see the cost until it's too late.
They understand your world. Not just your policy or your portfolio — your actual life. The business transition. The family dynamics. The new assets you're acquiring. The liability exposure that comes with the position you now hold and the profile you're building.
They bring you into their network. The right advisor doesn't just manage your file. They connect dots. They make introductions. They see opportunities you didn't know existed and put them in front of you at the right moment.
They are growing alongside you. The most valuable advisory relationships at this stage of your life are the ones where both parties are building something. An advisor who is ambitious, community-connected, and thinking about their own growth understands yours in a way that a transactional relationship never can. You're not a file to them. You're a relationship they're invested in.
The Insurance Conversation You Probably Haven't Had Yet
If you've recently stepped into a leadership position — in your family's business, in your professional life, or in your community — there is a specific conversation worth having about your insurance program.
Not because something is necessarily wrong. But because the policies that were designed for your parents' situation were designed for your parents' situation.
Your assets are different. Your liabilities are different. Your lifestyle and your risk profile have changed — and in many cases changed significantly in a short period of time.
The home you now own or occupy. The vehicles that reflect where you are in life. The professional liability that comes with the position you hold. The personal liability exposure that increases as your net worth and your community profile grow. The collections, the properties, the business interests that need to be reviewed in the context of who you are today — not who the file said you were three years ago.
These are not generic concerns. They are specific to the moment you are in right now. And they deserve a specific, honest assessment from an advisor who understands the full picture — not a renewal letter in the mail and a phone number on a card that nobody answers.
A Note on Relationship-Based Advisory
The advisors worth building with understand something that transactional service providers never will — that the relationship is the product.
Not the policy. Not the portfolio. Not the filing.
The relationship.
That broker's call stayed with me for a reason. Because at the end of the day — that is what this is about. Not the policy. Not the carrier. Not the premium. Whether the person on the other end of the phone believes that you will help them. That is the only thing worth building a reputation around.
An advisor who is genuinely invested in your success — who shows up, executes, tells the truth, and connects you to the right people at the right moment — is one of the most valuable assets you can have at this stage of your career and your life.
The second generation that builds the right team around them now will move faster, protect better, and compound more significantly than those who settle for the advisors they inherited.
You've been given the opportunity to build something of your own.
Build the right foundation under it.
About Maverick Insurance Brokers
Maverick Insurance Brokers is an independent private client advisory based in Brampton, Ontario. Founded by Bram Bains, Maverick serves entrepreneurs, business families, and community leaders across Ontario — providing direct access to a trusted advisor across home, auto, high-value assets, and commercial insurance. Maverick is a member of the MIB Broker Distribution Network and an official partner of the Brampton Honey Badgers (CEBL).
Maverick works with Canada's leading private client carriers — including Chubb and Intact Prestige— to deliver insurance programs built around the assets, lifestyle, and risk profile of each client.
Maverick Insurance Brokers has been recognized by Insurance Business Canada and Canadian Underwriter as a voice in the private client advisory space in Ontario.
for more information visit - maverickinsurance.ca
Book a Private Consultation with Bram Bains
If you're stepping into a new position of responsibility and haven't had a proper review of your insurance program — that conversation is worth having. No pressure. No obligation. Just a straightforward discussion with an advisor who is building alongside you.
