Jason Stubinsky

Partner | Financial Security Advisor

Jason has been working in the financial services industry since the late 90’s.

It all started back in Ottawa, when a local bank manager came into the restaurant where he was working and was seated in his section. A conversation ensued about banking and finance which turned into an invitation to interview. Thus began a two decade career working for one of the top chartered banks in Canada.

His time there included challenging roles within wealth management and business banking, where he helped many clients articulate their financial goals and take the next steps towards achieving them.

Many will remember him delivering market updates and empowering investors with ongoing wealth seminars and workshops in the Kingston, Belleville and Port Hope areas.

He has had the privilege of working with experts in the financial industry like Patricia Lovett Reid, Don Drummond, Bob Gorman and General Hillier, to name a few.

Jason’s greatest fulfillment was when a beautiful bank advisor at one of the local branches he frequented caught his eye and changed his life forever when she said ‘I do’. He is now a devoted husband and family man to his wife Stacie and 2 step children.

  • We required advice and feedback with respect to our growing business and were fortunate enough to meet Rick and Jason while attending one of their seminars. In subsequent meetings, they were extremely thoughtful and aware of our specific situation. We were very impressed with not only the amount of time they spent preparing, but also presenting, in a professional manner an appropriate strategy for us. They assisted in not only strategizing goals but provided a keen, practical awareness of methods to achieve those goals. We strongly recommend reliance on their expertise and advice. It was an exercise to which we did not initially look forward to, however, Rick and Jason made it a pleasant, enlightening experience and we look forward to working closely with them in the future. We highly recommend reliance on their advice.

    Michael and Ida Cotman
    M.W. Cotman & Associates Inc. Real Estate Appraisers & Consultants | Kingston, ON
  • Our insurance and investment needs were transferred to Jason earlier this year. We were immediately impressed with his knowledge and experience, but were even more impressed with Jason's interpersonal style. We are not wealthy, but were treated with respect and appreciation by Jason. We felt comfortable with him and confident that his engaging and warm style was a true reflection of him as a financial advisor. He took a considerable amount of time to get to know us, our future aspirations and our current financial situation. He then developed plans that met our individual needs and circumstances. Jason answered all of our questions completely. His presentation style was such that his suggestions were nonjudgmental, supportive and encouraging, making us feel confident as active players in the decision making. We know our investments and our future are in good hands. Caldwell Investments are fortunate to have Jason representing their firm.

    Fred and Wendy
    Kingston, ON
  • I was introduced to Jason 4 years ago; and my investment portfolio is so happy that I did - unlike my previous advisors and their lack of communication, Jason regularly keeps me up to date, advises me on how certain "financial decisions" will impact me not only today but in the future, and most importantly helps me understand the complexity of my investment portfolio. He takes a genuine interest in my financial well-being and he has helped me navigate through some complex financial issues… I would highly recommend him to anyone looking for a unique wealth management experience.

    Derek McCauley
    Royal LePage | Kingston, ON
  • At the risk of sounding overly dramatic, I can honestly say that I would not be where I am at today financially without the knowledge, insight and expertise of Jason. He has helped me open doors that I wouldn’t have thought were possible in a very short period of time. Throughout the process he has helped talk me through every deal we have done in a language that has been easy to understand in a sometimes, confusing financial world. I can say with 100% certainty that I will have a long and prosperous relationship with Jason and his team at Caldwell. Thank you, sir a ‘million’ times over.

    Andrew Burns
    Foundry Athletics/Foundry Adventures
  • We have been working with Jason for a number of years and have found him to provide clear and concise advice in a highly professional manner. He has spent time understanding us, where we are coming from and our goals; has provided clarity on our existing financial planning and has provided us with a clear strategy as to how we achieve the goals that we have.

    Michael Davidson
    P.Eng. | Black Diamond Engineered Products
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