About Us

I have been investing in real estate since 2012 and since that time have completed dozens of real estate transactions, a great majority of them by way of co-venture real estate investing. With a strong background working with families and organizations, I love learning about new investors, understanding their investment goals and objectives, and most importantly helping them build that pathway to success. In an effort to assist our growth I also obtained my Realtor’s license (caldwellrealestategroup.com) and regularly use that as a tool to service the investors I work with.

Our businesses have seen exponential growth over the last few years. My goal has always been to provide and create clean, safe and appropriate housing, and I feel fortunate that I have been able to do much of that in our local community while concurrently creating wealth for the investors that we have the privilege of working with. Additionally, I have been given the privilege of managing and creating our workforce of contractors and apprentices. I am thankful to them daily for challenging me, making me laugh and always digging deep when the going gets tough! Watching them grow, develop and learn while also creating our little ‘work-family’ has been better than I could have ever imagined and I am thankful every day for my “Dream Team”.

While real estate investing and the creation of generational wealth is a huge passion of mine, I also believe the power of connecting by unplugging. In my free time, you’ll find me spending time with Jeff, our three children and our family dog.

I also have a strong passion for the arts and with a background in creative writing I have finally committed to the next level and have partnered up with an editor and am in the process of writing my first novel in an effort to share, connect and inspire. Stay tuned!

Kelly Caldwell

We chose Dash as part of our business name based on Linda Ellis’ poem called The Dash, because it fits perfectly with the philosophy we hold – that of making the most of one’s life while we’re still living. Smart, calculated investing in real estate is an excellent way to ensure one’s financial future and to also create generational wealth. Begun early enough, investing in real estate also reflects The Dash because it can give us back the most important thing in our life – time to live your dash the way you want.

Kelly and I began our journey together as licensed funeral directors in the province of Ontario, providing assistance to hurting families as they said goodbye to the most important people in their lives. With that, we have also witnessed and listened to the regret many shared over relationships not fulfilled or experiences not lived, and those stories have become part of our story in helping others live their dreams and enjoy this life.

For the last 23 years I have enjoyed the privilege of teaching at Humber College in Toronto, in the program that prepares individuals for licensing as funeral directors. I also serve as Manager of North American teams for Blake Emergency Services, an international crisis response and contingency planning company based in the UK. For the last 10 years Kelly and I also been investing in real estate and now have a substantial portfolio of investments and properties throughout North America. Very close to retirement now, I look forward to working full time beside Kelly.

Jeff Caldwell