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Doug Leyland

Founder, President · CPA, CA, MBA

Portrait of Doug Leyland
Leyland & Matters CPA, CA, MBA

A career built on independence, experience and putting clients first

In the year 2000, I made what turned out to be the defining decision of my career.

Things were going well at a well-known U.S.-based investment dealer, but I was becoming increasingly frustrated with being told by management which proprietary products I should sell to my clients. I resisted. Many of these manufactured products made money for the firm, but I wasn’t convinced they were always the best solution for my clients.

I came to believe that when a financial institution both manufactures financial products and sells advice about those products, there can be a conflict of interest. So I left and started my own investment firm, yourCFO Advisory Group, along with a life insurance and living benefits company, yourCFO Insurance Solutions.

It was not an easy decision or an easy undertaking. But I wanted the names to reflect what mattered to me: putting the client’s interests first and bringing the expertise needed to help families make good financial decisions.

Over the years, I came to appreciate just how interconnected the various pieces of a family’s financial life really are. Investments, taxation, estate planning, business interests, succession and life insurance don’t exist in separate boxes. Decisions in one area can have a profound effect on another.

That understanding is particularly important when it comes to permanent life insurance.

Today, my professional focus is life insurance, particularly permanent insurance used in estate planning, wealth transfer, business succession and other sophisticated planning strategies. While I no longer act as a wealth advisor, I bring nearly 40 years of experience in wealth management to my work with insurance clients. I believe that background is a significant advantage when determining how life insurance should fit within a client’s overall financial picture.

Permanent life insurance can represent a substantial financial asset. It needs to be considered alongside a client’s investments, tax situation, estate, business interests and long-term objectives. Understanding the investment side of a client’s balance sheet helps me ask better questions about why insurance is being considered, how much is appropriate, how it should be structured and how it should work with the rest of the client’s financial plan.

My road to this work started in Burlington, where I grew up and where, from childhood, I have always been entrepreneurial: paper routes, cutting lawns and shovelling snow back in the days when we had snow.

I graduated from Nelson, where I made many lifelong friends and learned an important lesson: I would have to work hard and smart to make my way in the world. After upgrading my marks, I went to Wilfrid Laurier University and earned an Honours BBA. Business interested me, but I was already beginning to figure out what I did not want to do with my career. I didn’t see myself spending my life in the corporate world.

I turned toward accounting, thinking it would be a great way to learn how family businesses work. I was right. After articling with Clarkson Gordon, now Ernst & Young, and obtaining my CA, I decided that a life in public accounting was not in the cards either. So it was on to McMaster University for an MBA, still trying to decide how I wanted to spend the next 50 years or so.

Through a family connection, I eventually found myself in the Wood Gundy training program. It was the second week of October 1987 when the stock market crashed. It wasn’t exactly an ideal time to start a career in the financial world, but I decided to give it a shot.

My thought was simple: I could build a client base and use my financial and tax knowledge to help families build plans to grow and protect their wealth. Over the following decades, I had the privilege of doing exactly that.

The experience was invaluable. I saw firsthand how families and businesses were affected by changing markets, tax laws, economic cycles and major events. We navigated through the 1987 crash, 9/11, the technology meltdown, the financial crisis of 2008 and 2009, and, more recently, the upheaval brought on by Covid.

Those experiences reinforced something I have believed throughout my career: financial planning isn’t really tested when everything is going well. It is tested when things become uncertain.

The world can be a scary place at times, and like a good airline captain, we all need that calm voice when things get a little bumpy.

In 2014, my partner Jordan Matters joined me. You will have to meet Jordan to appreciate what a knowledgeable, talented and outstanding person he is. Together, we have built an independent insurance practice where our focus is on helping clients make thoughtful decisions about life insurance and how it can support their families, businesses and estates.

Today, we conduct our life insurance business through Leyland & Matters, using TruStone Financial as our Managing General Agency. We enjoy the independence that allows us to look across the marketplace and focus on finding solutions that are appropriate for the client rather than starting with a particular product.

Throughout my career, I have also had the pleasure of serving our community. I chaired the Leadership Group of the United Way and, while doing so, had the pleasure of having hockey legend Bobby Orr, a client, act as honorary co-chair. Everything you have heard about Mr. Orr is true. He is a true gentleman and one of the nicest people you could ever meet. I have also served on the Investment Committee of the Burlington Community Foundation.

And on a personal note, in 2013, alongside my children Andrew and Claire, I climbed Mount Kilimanjaro.

As the mountain guides say, pole pole in Swahili: slowly, slowly.

It is good advice for climbing a mountain, and I think it is good advice when making important financial decisions too. There is rarely a prize for rushing into a major financial decision. The best strategies are usually the result of taking the time to understand where you are, where you want to go and how all the pieces fit together.

After nearly 40 years in the financial services business, that is still what I enjoy most: helping people make important decisions with confidence, and using my experience to help make sure the life insurance strategy we put in place serves a much larger purpose.

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