Cudmore Ross Wealth Management - Who we are

Stephen Cudmore BBA, CFP, FEA

Senior Wealth Advisor, Branch Manager

I’m a lot like my dog, Jordie. He’s a Portuguese Water Dog, bred to herd fish into nets, retrieve lost tackle, and act as a courier from ship to ship or ship to shore. Jordie, like me, is indefatigable. He swims powerfully and he does not shed.

Everything else about me is straightforward. I’ve been a wealth advisor since 1992, starting in Toronto, after an initial career in the grocery business. It was there that I learned about the importance of customer service, competitive pricing and human psychology.

People are people, however much they’re worth. They want respect, recognition and a fair hearing. Listening skills, which I have, are hard to teach. As is the capacity for client rapport. I can be outspoken, but that’s a reflection of my continuous quest for results.

Money isn’t funny. Making it and keeping it takes hard work, and experience. I earned my Canadian Securities designation with Honors, specializing in meeting the wealth management needs of high-net-worth families.

I’m certified in Financial Planning, Insurance and Estate planning, and Options Supervision. For over 10 years I was Vice President and Branch Manager for one of Canada’s largest bank owned investment dealers.

In 2014, I became a Branch Manager of Richardson Wealth for Atlantic Canada ($1 billion+ in assets under administration) and currently manage one of the largest wealth management practices in Prince Edward Island, specialising – though not exclusively – in the needs of small business owners.

In 2022, I earned my Family Enterprise Advisor designation (FEA). The FEA is one of the leading designations in the world for helping families of significant wealth navigate the complexities of transitioning that wealth to the next generation. I’m what they call a seasoned professional.

Though born in Halifax and raised in Prince Edward Island, my formative professional years were spent in Toronto. The pull of the PEI landscape, beaches and – most important – the people drew me back here in 1996. Since then, whatever residual Toronto pushiness I subconsciously acquired while working there has been progressively kicked out of me.

I’m active in the community, which I feel is both a pleasure and an obligation. A very successful client once told me that giving back is the rent we pay for the privilege of living here.

Past chair for the Fundraising committee for the Summerside Wellness Center.
Past chair of the Fundraising committee for the Summerside Rotary Inspire Learning Centre.
Past president of the Rotary Club of Summerside.
Past chair of the PEI Easter Seals Campaign.
Past board member of the Holland College Foundation.
Past Vice-President of the PEI Alpine Ski Team.
Multiple Paul Harris Fellow in Rotary.
Long standing member of the Atlantic board of Canadian Investment Regulatory Organization.
Past Commodore of the Charlottetown Yacht Club.
Founder of the PEI Boating Festival.

I’m married to Michelle. We have two university age daughters Makena and Macy. As a family, we love skiing, sailing, hiking, travelling, and walking our Portuguese Water Dog – with whom I am occasionally confused.

Jonathan Ross BBA, PFP

Senior Investment Advisor, Assistant Branch Manager

I wear a bow tie. It is an important clue both to my character and to the way I work. Like so much in successful wealth management, tying a bow tie requires the mastery of several delicate steps, all of which must be accomplished with the utmost dexterity. It is said that less than 1% of adult men know how to tie their own bow tie. I am one of them.

In the investment management business since 1999 and I partnered with Stephen Cudmore in 2004 to form Cudmore Ross Wealth Management. My responsibilities include, but are not limited to, selecting assets, implementing plans and monitoring investments to achieve our clients’ specified investment goals.

A Bachelor of Business Administration from the University of Prince Edward Island, I am a recent graduate from the Securities Institute at the prestigious Wharton School of Business.

I am active in the community:

Past president of the Hillsborough Rotary Club and multiple Paul Harris Fellow.
Past president of the PEI Community Foundation and chair of the Investments Committee.
On the board of directors and board of management for the 2023 Canada Games host society.
President of the Charlottetown Executive Association.
Past board member and chair of the provincial advisory board for Heart and Stroke Canada.
Past commodore of the Charlottetown Yacht Club and chair of Charlottetown race week for several years.
Charlottetown Citizen recognition award in 2012.

I live in Stratford with my wife Emma, and our two children, Dexter and Summer.

Luanne Coady

Associate

There are three fundamental skills necessary for successful administrative and project management: technical, human and organizational.

You must understand the issues you’re handling. Like my colleague Julie, I have completed the Canadian Securities Course from the Canadian Securities Institute, so I do. I’m project proficient, particularly in tax management. Accountants like working with me and I like working with them.
You must be able to function well with people, both those inside our practice and those visiting us. A talented administrator interacts with many individuals during a working day, including clients and colleagues. So-called soft skills count. I have them.
You must be a skilled time-manager, adept at prioritizing tasks by deadline and being pro-active, adaptable, accountable and super-efficient, while never losing your cool.

I began working in the investment industry in 1998, joining Cudmore Ross Wealth Management in 2014. My job, above all, is to forge professionally productive yet never less than friendly relationships with all those with whom I deal.

Along with being known as a no-nonsense team member, I’m funny. I play practical jokes on people. Along with Jonathan, I am chief strategist for the annual Cudmore Ross Wealth Management April Fool’s Day escapade.

Jeremy Dewar

Assistant

My previous work in casino gaming gives me an unusually acute edge.

The ability to think probabilistically is the key. Probabilistic thinking is a useful way to reach viable conclusions in an uncertain world. It informs effective decision-making and helps manage risk.

This capacity helps me understand the important work that Stephen Cudmore and Jonathan Ross do for their clients. They make the decisions - I help organize their professional lives, so they make the right ones.

Cars & Insurance

After graduating from the University of Lethbridge, I worked various occupations including automotive sales and insurance claims. Both offered solid training and an interesting set of new skills.

In the former, I learned the importance of building relationships, financing terms, negotiation, and the art of the deal.

From the latter, I learned to investigate losses, interpret insurance policies, determine liability, and maintain accurate and updated records.

Croupier

Working as a Croupier (officially a Table Games Dealer) was both an escape and an inspiration.

I rapidly mastered the art of dealing fast-paced and entertaining games of Blackjack, Baccarat, and Texas Hold’Em.

Important insights acquired: 1. Manage your bankroll. 2. Minimize losses and maximize profits based on changing conditions. 3. Make rapid and accurate calculations. 4. Learn from the best.

All these skills are directly relevant to the work I perform at Cudmore Ross Wealth Management, especially point 4 – which is why I’m here.

Personal

Apart from my work in wealth management, I am an avid supporter of the Toronto Maple Leafs. Go Leafs go!

Macy Cudmore

Business Development Assistant

My name, Macy, has roots in Old French and once meant “weapon” — a tool designed with intention and precision. In wealth management, I see that as a metaphor for thoughtful strategy: not about force, but about being equipped with the right tools to help clients navigate complex financial landscapes.

At Cudmore Ross Wealth Management, my focus is on uncovering value — whether in overlooked opportunities or in building plans that reflect what truly matters to each client. I believe strong financial advice begins with listening, and that clarity and trust are just as important as performance.

Previously, I worked for the Government of Prince Edward Island in various offices. In the Executive Council Office. My work involved investigating a 43-year-old systematic problem in communication and decision-making to produce solutions to top decision-makers for the province. In the Department of Finance, I analyzed institutional money managers to ensure the efficient money management of Islanders pensions. With the Department of Economics and Statistics, I conducted a comprehensive assessment of PEI’s economy relative to the other provinces and developed budget recommendations to ensure the strength of the Islands varying sectors.

After that I worked as an investment analyst for Xaverian Capital. Based in Nova Scotia, my job at Xaverian Capital was to work with my peers to manage a student-run investment fund. This investment fund was and remains premised upon value investing, aimed to drive capital growth and ensure capital preservation, the twin pillars of wealth accumulation. Our job was to analyze companies on the TSX to determine if they aligned with our investment philosophy and allocate capital accordingly.

Before joining Cudmore Ross Wealth Management, I worked at the Royal Bank of Canada, Global Asset Management as a Summer Analyst on the North American Equities, based in Toronto. My principal responsibility was to construct financial models for several companies in varying industries. This led to the presentation of my findings to managing directors and senior portfolio managers at our asset management group.

Bottom line? I learned to analyze, listen and communicate.

Beyond work, I am pursuing publishing my research on the impact of artificial intelligence in financial services. For leisure I enjoy outdoor activities all year round from sailing during the summer months and skiing during the cold months. I am a former athlete and in my spare time enjoy activities that light up my competitive side. One of my biggest joys in life is reading a good book.