How I Chose to Invest in Real Estate - Riley Oickle

One of the most common questions I get these days is why I chose to invest in real estate out of so many options out there. Quick answer - it is by far the best vehicle to build long-term wealth and financial freedom. After all, real estate is the type of asset you can control, unlike stocks and some of the other options out there. Having that control over what you put your money into is what attracted me to start considering RE investments. However, I feel like my journey toward entrepreneurship began way before I even stepped foot in the real estate industry. Here’s how it all started.

Early College Days

If I could tie it back to one particular time in my life when things started to shift in my work ethic, I feel like that would be during my track and field days at college. That’s when I started to really focus on delaying gratification and setting goals for the future. Mind you, I was in a very small town of a few thousand in Nova Scotia. 

My coach back then was actually a coach on Team Canada for track and field, a really phenomenal coach who understood psychology and how to inspire someone and have them push past their boundaries. The cool thing about track that has helped me a lot in entrepreneurship and running my business is the balance between running for yourself and trying to beat your personal best (you’re competing with yourself) but also you’re in a team competing for points so your entire team wins. In that sense, there is an individualistic component but also a team component as well. 

I was working so hard back then that I even got a scholarship to go and run track and field at a university in Ontario. I left Nova Scotia and came to run track and field at the Ontario university and I did pretty well. However, I wasn’t the best like I used to be in Nova Scotia where I would win medals and be on the podium quite often. That’s where I faced my first frustration - the idea that I’m not the best at this - naturally so. Through university, I was realizing I’m running into a lot of debt. I didn’t have a great paying job and I needed to make money.

First Business Opportunity

I once came across an opportunity that said “sign up here to learn more about how to make 50 000 dollars this summer” Before then I worked at a grocery store so 50 000 seemed like a lot of money. I went to an information session to learn how to run my own home maintenance company. This organization helped university students run their first business - that’s where I started my journey. I applied and was selected - they appointed me a business coach with whom I worked for over two years. During the first four months, I made over 25 000 and I never wanted to go back to being an employee. I learned about the results-based economy where you get rewarded for the results you put forth and this seemed like the right way to go. I became obsessed with how to make my own time more valuable and I ended up doubling the business to 112 000 in the second year when I employed 12 students.

Between the first and the second year, I covered the entire cost of university (4 years) and I bought myself a vehicle. The transitional point was in the third year when they offered me to start coaching students to do a similar thing. That’s when I started teaching and shaping leaders, which became my obsession for the next three years. After I left the company, I still kept operating my business, which I turned into a corporation operating in Southwestern Ontario even to this day.

Transition into Real Estate

Working in the home maintenance space allowed me to get more insight into how properties are structured and what kind of work they require. I learned how to work with contractors and how to be one. This experience helped me transition into buying houses.  Eventually, I learned more about the importance of assets and I quickly realized that I needed to stack some up to be able to get bank loans whenever it was necessary for my other business ventures. 

That’s when I connected with a coach who had done over 15 million dollars in real estate and, under some lucky circumstances, he happened to be looking for an assistant at that time. I managed to get that position and I started learning about real estate through my work with him. This opportunity allowed me to get a real shot at managing over 100 tenants and see what it’s like to be a part of the real estate industry. This was my foot in the door opportunity. 

I was going through the trenches as much as I could to learn the details of how everything worked because I knew that if I’m gonna buy properties like he’s doing, I need to understand these roles well so ultimately I can find people to fill these roles and be able to manage them really well. During the following months I spent a ton of money on coaching and educating but the problem was that I didn’t have the mortgage capability to purchase a property. That’s when an opportunity came up for a JV to get a small single-family property in Sarnia, which happened to be my first one.

Even to this day, joint ventures are one of the most common ways for people to enter the real estate space, especially if they don’t have enough of their own capital stacked up.