Welcome to Theodor Hennessey & Ross
Private Wealth Management
Your financial life isn’t just about investments or savings; it’s a web of interconnected pieces that need to work together seamlessly. At Theodor Hennessey & Ross, we do more than advise. We’re here to untangle, simplify, and align your financial life so it flows seamlessly toward your future. Whether you’re protecting your business’s legacy, optimizing your retirement, or ensuring your wealth spans generations, our expertise delivers clarity in the chaos.
Exclusive, tailored relationships
We’re selective. Serving fewer clients means serving better. High-net-worth families, business owners, and those with goals worth protecting deserve our undivided attention. Your wealth, your values, your aspirations—this is what shapes every plan we design. It’s not about us. It’s about building something that reflects you.
Expertise you can rely on
At Theodor Hennessey & Ross, we bring an uncommon advantage: legal expertise integrated into our financial planning. One of our financial advisors is also a lawyer, allowing us to offer unparalleled insight into estate planning, wills, and tax strategies. This level of detail ensures your plan is not only comprehensive but also resilient—giving you confidence that every angle is covered.
Long-term stability for your financial plan
Your financial journey deserves continuity. Our team is young enough to stay by your side for decades, ensuring your plan evolves alongside your life. We combine years of experience with the energy and commitment of a team dedicated to seeing your goals through from start to finish. You won’t have to worry about transitioning your plan to someone new; we’re here to provide stability and consistency every step of the way.
A business owner’s perspective
We know what it’s like to lead a business. The pressure. The sacrifices. The decisions that keep you awake at night. As business owners ourselves, we don’t just understand your challenges—we live them. From corporate tax optimization to succession planning and cash flow strategies, we bring insights born from experience. It’s not theory; it’s a shared understanding.
Building generational wealth that lasts
Preserving and growing your wealth isn’t just about today—it’s about creating a legacy that endures. We specialize in generational wealth strategies, helping families pass on not just assets but also values. Whether it’s funding education for future generations, structuring trusts, or creating a philanthropic impact, we craft plans that adapt as your family’s needs change over time.
Tax efficiency at every step
Taxes are relentless, but they don’t have to steal the show. Every withdrawal, every allocation, every credit—we make it work harder for you. Whether it’s splitting income, timing withdrawals, or leveraging tax opportunities, we ensure every dollar serves your goals.
What we do
At Theodor Hennessey & Ross, our wealth management services don’t work in isolation. Every piece—your cash flow today, retirement strategies for tomorrow—fits together into a living, breathing plan. This isn’t financial planning on autopilot. It’s dynamic, purposeful, and built to adapt as life does. Every service we offer is part of a bigger vision: making your wealth work harder, last longer, and mean more. Let’s build your future together.
Insurance planning
Life isn’t predictable, but your financial safety can be. We craft protective layers—life insurance, critical illness insurance, disability insurance—designed to shield your wealth and your loved ones. Every policy is tied to your goals, aligned with your lifestyle, and ready to step in when the unexpected happens. It’s not about bracing for the worst; it’s about having the confidence to live fully, knowing your financial future is protected.
What our clients say
I have worked with John and now Laurel for 27+ years, and for my wife and I, it has absolutely been the right choice. I sleep very comfortably at night knowing that all my financial needs have been thoroughly considered and my plan for the future has been well thought out and solid. John has regularly reviewed my personal situation and advises, in a timely fashion, any needed adjustments to both my portfolio and my financial plan. We meet regularly or chat by phone to keep up with changing financial markets, take advantage of new financial government programs, or just to catch up. I can’t imagine anyone else doing a better job!
- Frank M.
John Ross has been our trusted advisor for over 25 years. He has guided us from the beginning as a young married couple, to the busy family that we are today. He has addressed our retirement, insurance, RESPs and other unique needs throughout this journey with expertise and professionalism. We are beyond pleased with our investment portfolio, and the service level provided has exceeded all expectations.
Karin E.
Mike and his team have been great to work with. As an entrepreneur, I like to be razor-focused on the success of my business and not worried about money management. That said, I recognize the vital importance that smart financial planning has in ensuring my family is set up comfortably for the years to come. Mike and his team have been true professionals in helping me structure my corporation strategically and recommending savvy tax planning solutions. It's been comforting working with a team I trust and to feel confident I have the best long-term plan for growing my wealth.
- Cam M.
Konstantine’s vast knowledge coupled with extraordinary service is rare in the financial industry… or any industry. Initially, he deftly guided our family through my mother’s estate account and continues to do so. He also now assists my husband and myself in managing our retirement funds. If we have a question, Konstantine responds immediately and if necessary, follows up with any concrete action, no matter how complex or simple. He continually reaches out to us to ensure our absolute satisfaction and warmly welcomes any communication we initiate through email or phone which is so reassuring. Konstantine is utterly dedicated to ensuring the best outcomes in every situation. A genuine, honest, kind human being who takes his responsibilities for his clients’ financial welfare to heart, we feel we have ‘struck gold’ on many levels!
- Sharon P.
Konstantine has been my financial consultant for 5 years and has consistently provided me with exemplary service. From our initial meetings I was impressed with his very personal approach and his ability to translate complex concepts into concise and easily understood solutions. As a business owner I have very little time to waste and so I appreciate his team’s attention to detail and his presentation of material in a clear and concise manner. He conducts himself with the utmost professionalism and comes extremely prepared to all our meetings. I would and have recommended him without reservation.
- Joseph D.
CEO of TransportCorp
We have worked with Konstantine and his group since 2019. During that time we have received excellent client service. Specifically, we have been impressed by his ability to listen to our concerns and his ability to accurately gauge our tolerance of financial risk. He articulates options in a clear and understandable manner without ever talking down to us. We especially appreciate his proactive and timely approach to customer service as he regularly checks with us and is on top of important decision-making timelines. We have a respectful and professional relationship with him.
- Mary L. & David C.
Mike and Konstantine, I am absolutely delighted with your service. It is refreshing to work with financial advisers who are truly interested in their client’s needs, circumstances, and preferences. What really impressed me was the way you took the time to get a feeling for where I was and what I was trying to accomplish, your depth of knowledge, lateral thinking, and common sense approach. I have never had this kind of experience in the past with financial advisers and this is the kind of service I have been looking for. It’s nice to have one place to come to, without it feeling too large or institutional. They always explain everything thoroughly and I never feel uncomfortable asking questions or expressing an opinion. I feel like you know the whole picture and if anything happened to me now, I know my family will be well looked after.
- Bette U.
Jane and I are very pleased that we have handed our retirement dollars into the trusted and capable hands of Konstantine. Konstantine has spent unhurried time with us, explaining the various aspects and requirements of our funds, in the areas of banking, investment, government requirements and so on. His presentations to us have been clear and simple to understand even when complex matters are being considered. Working with Konstantine is a pleasure, and the interest, work and sustained positive results have been a blessing to us, especially in areas where we have had little understanding of in the past.
- Jane & Laurence B.
I have known Teresa for almost 15 years. During this time, I have found her to be a dedicated professional, honest, discreet, and does her best for me at all times. She assists me with all aspects of my personal finance, including liaising with my lawyers and accountants. She is also utterly reliable, always available, and importantly, has become a good friend. I don’t know what I would do without her.
- Gloria
I have developed growing confidence and respect for Teresa over the last 20 years or so as my financial advisor. She has provided intelligent explanations and thorough discussions about the markets and allayed my fears when needed. In addition, she has provided me with confidence to transfer funds from my bank’s mutual funds to IG. The annuity I purchased has also proven to be invaluable. When I feel confused or distressed about the market, her patience has been greatly appreciated. As I’m a widow now with grown children and need to make wise decisions about my vacation plans, retirement assets, and bequests, these are all topics I can freely discuss with Teresa. I would be remiss if I didn’t highlight her personal concern for me as a client. In sickness and in health, she has provided superior kindness and generosity with her time. As my sons and their partners have chosen to join IG, they too have benefitted from a lowered advisory fee. Anyone considering Teresa Loy and IG would have their expectations honoured.
- Karen
Almost 20 years ago, a mutual friend introduced me to Teresa Loy. From our first meeting to this day, Teresa has managed the Financial part of my affairs. Her expertise, knowledge, sound judgement, attention to detail and caring nature combine to make her the best in her field! She is a valued member of my "Family"!
- Sylvia S.
Konstantine’s vast knowledge coupled with extraordinary service is rare in the financial industry… or any industry. Initially, he deftly guided our family through my mother’s Estate Account and continues to do so. He also now assists my husband and myself in managing our Retirement Funds. If we have a question, Konstantine responds immediately and if necessary, follows up with any concrete action, no matter how complex or simple. He continually reaches out to us to ensure our absolute satisfaction and warmly welcomes any communication we initiate through email or phone which is so reassuring. Konstantine is utterly dedicated to ensuring the best outcomes in every situation. A genuine, honest, kind human being who takes his responsibilities for his clients’ financial welfare to heart, we feel we have ‘struck gold’ on many levels!
- Sharon P.