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SIMON HALE & MICHAEL HALE, Senior Wealth Advisors, Hale Investment Group, Wellington-Altus Private Wealth, Montreal, Quebec


"Quality from the ground up"

Simon and Michael Hale are brothers who share a passion for finance and supporting a client’s financial success. They know that an understanding of finance doesn’t come naturally to everyone, so they have a unique ability to explain complex matters in a simple-to-understand fashion.

Whether it’s telling a story or using an analogy with which a client will be familiar, the brothers are focused on providing open, transparent communication from the very first meeting. It’s the foundation of their business.

Simon and Michael believe that the key to success is integrity, hard work, and discipline; they are values instilled in them from an early age, and through all their successes, remain as vital today as they were then.

Strong roots

Simon and Michael grew up in a small village in rural Prince Edward Island. The population at the time? Around 100. Their neighbours were fishermen and farmers, truly kind, genuine, hard-working people. It was a unique upbringing, which informed much of how the brothers conduct business today.

Their enterprising spirit is not a new development; Simon and Michael started their first business venture when they were each younger than 10, on top of their regular attendance at school. The brothers secured a contract to do landscaping work at a local cemetery. The only problem was that they didn’t have the tools to do it right. “Our dad bought the lawnmower for us,” Michael said. “We were happy and excited, and we thanked him for helping us. But he wasn’t giving us a gift. He was teaching us our first business lesson. He wrote a contract, and we paid him back over time. I don’t recall him charging us interest, but it was a real lesson: You need to invest money, to make money.”

And make money the brothers did. They expanded the business and started cutting lawns for their neighbours and parent’s friends. For a pair of kids, they quickly became flush with cash, and they needed a way to invest it. Their mother took them to their local Credit Union to invest in savings bonds, and for Simon, it’s what sparked his passion for investing.

“When you’re nine or 10 years old, and someone tells you that if you invest $100, after a certain period of time someone is going to give you $110 back, it’s life-changing,” Simon said. “It sparked a fire inside me that’s still lit to this day. Taking something and making it grow is one of the most satisfying feelings there is in this world, and it’s been my calling ever since.”

The lawnmower and its important lesson wasn’t the only one their father imparted in their youth, either.

Their father also taught the brothers about the importance of a strong foundation, and the philosophy of “anything worth doing, is worth doing right. There are no shortcuts.”

He was a craftsman who took immense pride in everything he did, whatever it was because he always gave his best effort. It’s a philosophy that the brothers have adopted completely. The philosophy has allowed them to remain grounded, despite their successes, and never forget that they are working for clients, and not the other way around.

Luck is when opportunity meets preparedness

Simon’s dream was to work in finance, but there were no opportunities to pursue it in his village. He needed to range far from home to make his dream a reality. He found himself in Montréal, one of Canada’s most vibrant and cosmopolitan cities. Simon knew he could build a career there, but it wasn’t going to be easy. He knocked on a lot of doors. Most of those doors were closed to him, but he was undaunted. Every no fueled his desire to find a yes.

Through his effort, he met the right people, and he was able to find his way into a rewarding career. It was a difficult start, but he persisted. There’s no quit in Simon. “I remember when I first started, I had this old Nissan Sentra, and it stuck out like a sore thumb. It was hideous. Before client meetings, I’d hide it because I didn’t want anyone to see this monstrosity I was driving. I think back now and laugh about those long walks, but I remember the lesson they taught…the only difference between a big shot and a little shot is that a big shot is just a little shot that kept on shooting.”

Simon was having success in the thriving Montréal financial scene, but he felt like something was missing. He needed a partner. A partner with whom he could build his own business, instead of someone else’s.

He needed his brother.

Simon and Michael have always been close, no matter the geographic distance between them. In the mid-2000s, the brothers took a trip out west. It was an adventure vacation, a trek through the mountains. It was during this trip that Simon broached the subject of working together.

At the time, Michael wasn’t working in the investment industry. He was working in international business, spending five years in Los Angeles, and six years in China. It was years of challenging work, but he was happy doing what he was doing…though the opportunity to work with his brother was tempting.

The pair knew what they could do when they worked together, and Michael jumped in with both feet.

“As soon as Michael joined me, there was no stopping us,” Simon said. “We each have our strong suits and a unique set of skills. When he and I work together, our efforts compound like a great investment.”

Foundation of Success

When they started in the business, it was all about selling; investment pools, stocks, bonds – build a relationship with a client, then sell them investments. They were fundamentally good investments because the brothers cared about every client, but it was still a sales job. It didn’t excite the brothers the way those first trips to the credit union did.

They worked hard, eventually becoming portfolio managers – it was a decision they’ve never looked back from, because it was exactly the type of work Simon envisioned when he was a kid.

With their experienced team, they manage a vertically integrated wealth management practice. They start with financial planning; they will review asset allocation, doing all their own research, they even have a dedicated trader on their team to facilitate the process. It’s a lot of extra work, but the brothers feel a responsibility to give everyone their best effort because their system sets every client up for success.

“We’re proud of our proprietary portfolio management process,” Michael said. “If you want to be great in this industry, we feel like you need to take full ownership of the entire process. You live and die by your work. Simon and I aren’t perfect, but where we excel is our adaptability. If the facts change, we change along with them, making the best decisions for clients as we go. Every choice we make is predicated on the best result for the people we serve.”

One of Simon and Michael’s key differentiators is how they view investments. Often, people in the financial industry only see commodities; stock prices that go up and down. The brothers see things very differently.

“When Michael and I talk to clients about what they own, we aren’t talking to them about stocks. We’re talking to them about the companies they're invested in. It’s a different mindset altogether. I will say to clients, ‘Look, this business creates a product that’s great – I use it, you use it, and here’s where we think this business is going.’ It’s quite different than looking at a stock and saying, ‘We expect this stock to increase by such and such a percent by Q4 2025 because of a stronger than expected Q1 earnings.’ Lots of organizations do it that way, but it isn’t how we operate. Me and Michael are looking to build something; something real, something tangible. It starts with our unique perspective on the business, and it shows in our results.”

Our whole team is always there to help in a professional and friendly manner. When clients call or write to us just to say thank you for giving them peace of mind, or for helping their family through a stressful event, that’s what drives us. At the end of the day, it’s what makes our job most fulfilling. Not simply putting up good investment results, but actually making a difference in our client’s lives.

Gary Milakovic is a veteran writer with more than a decade in the public sector and corporate communications. He has covered a wide spectrum of topics and his work has been featured by large and small organizations across Canada. Gary is passionate about communication, his writing often focuses on uncovering the “story behind the story.”

Simon Hale CIM®, CIWM, FCSI®

Senior Wealth Advisor & Portfolio Manager


Michael Hale CIM®

Senior Wealth Advisor & Portfolio Manager



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