Kelly Caldwell

What business / career achievement makes you proud?

Purchasing my first investment property in 2013, I have now grown my portfolio to over 40 doors across the province. Building from the ground up I am now the co-owner of a local real estate investment company, property management company and contracting company that services Collingwood and surrounding areas. Having recently been the recipient of the Keyspire 8 Figure Achievement Award, I am honourd to be a part of not only the development of my power team, but also a support for my investor clients, whether new or experienced. I find great satisfaction in inspiring investors to take action and showing them how to overcome their perceived obstacles. As an advocate for clean, safe and appropriate housing options within the community, my recent appointment to Collingwood’s Affordable Housing Task Force brings a new and exciting challenge. Being appointed to work with this incredible team has not taught me much about county, municipal and social housing challenges but has also opened up a new and exciting opportunity to play a small part in creating road maps that lead to the creation of housing solutions within the community of Collingwood.

What is the most challenging thing you have ever done?

As the oldest of three children growing up in a single parent, low income household was a challenge to say the least. Our family struggled to put food on the table weekly and we often found ourselves without basic necessities; hot water or power to our home because we simply could not afford to pay the bills. After my father died unexpectedly when I was 21 years of age, I found myself being told that I was now the legal guardian of my two siblings who were still minors. With no other options, I was forced to apply for subsidized housing. The social worker assigned to us went above and beyond her job description and not only expedited housing options for us but also arranged movers, grocery delivery, lease agreements, etc on our behalf. On move in day, I remember vividly asking her “how can I ever pay you back for this”? Her response changed the trajectory of my life when she said “I don’t want you to pay it back. When you have an opportunity, I want you to pay it forward”. Figuring out exactly how I would do that took several years, but once I was able to figure out the power held in real estate investing from a strategic level, I was not only able to change my own life, but also impact hundreds of other lives across the province. With great challenge comes great rewards. Standing on the other side looking back, the most challenging time of my life has turned into the most powerful took I have ever utilized and it is my hope to continue to pay it forward by empowering others through education and the creation of investment and housing options.

What is your favourite book?

Start With Why: How Great Leaders Inspire Everyone to Take Action