In the latest addy podcast episode, our co-founder, Stephen Jagger, sits down with real estate investor Riley Oickle to dive into his inspiring path from student debt to building a multifaceted real estate portfolio. Riley shares insights into his unique journey, from early entrepreneurial ventures to leveraging advanced investment strategies. Here are some highlights—and if you’re ready to dive deeper, check out the full episode on our YouTube channel or listen on your preferred podcast platform( Spotify, iTunes and Google Play).
Humble Beginnings: Building from Scratch
Riley’s story began not in real estate but with a job at a grocery store and later as a university student burdened with debt. Determined to pay off his loans, Riley launched a home maintenance business, gaining valuable skills in management and client relations. By the time he graduated, he had built a six-figure business, which served as a stepping stone into real estate. Reflecting on this period, Riley shares how his experiences taught him the fundamentals of business that continue to fuel his success today.
Discovering Real Estate Through Client Insights
As his home maintenance business flourished, Riley worked with several real estate investors, sparking his own interest in the field. Encouraged by clients who owned rental properties, Riley took his first steps by learning the ropes from a local investor. “Getting behind the scenes of someone’s portfolio helped me understand the mechanics of rental properties,” Riley recalls. This hands-on experience was invaluable, as it gave him a practical understanding of property management and tenant relations.
First Purchase and the BRRR Strategy
Riley’s first real estate purchase was a single-family home that needed extensive work—a project he undertook with a partner. This initial venture introduced him to the BRRR (Buy, Renovate, Rent, Refinance) strategy, which has been central to his investment approach ever since. “The smell of nicotine was everywhere, but I saw it as an opportunity to add value,” Riley notes, highlighting how he transformed the property through strategic renovations.
The BRRR strategy became Riley’s cornerstone: he could recover a large portion of his capital by refinancing the improved property, enabling him to reinvest in additional properties. This cycle allowed him to build his portfolio methodically, even as a young investor in the competitive Ontario market.
Scaling Up with Multifamily Properties
As Riley gained experience, he shifted focus from single-family homes to multifamily units, aiming for economies of scale. By consolidating multiple units within single properties, he found it easier to manage operations and maintain cash flow. Today, his portfolio includes a variety of multifamily properties across multiple Canadian markets, diversifying his holdings and providing a steady foundation for further expansion.
Exploring Short-Term Rentals and Land Flipping
In addition to long-term rentals, Riley has explored other avenues, such as short-term rentals and an innovative land-flipping strategy. While short-term rentals required careful management and adherence to regulations, the land-flipping strategy provided him with flexibility and liquidity. Riley’s approach involves purchasing large rural plots, subdividing them, and either selling or developing the land—a strategy that offers faster returns and adapts well to fluctuating market demands.
Looking Ahead: What’s Next for Real Estate in Canada?
In his conversation with Steve, Riley shared his thoughts on the future of Canadian real estate. He emphasizes the need to adapt strategies to market conditions, particularly with rising interest rates and changes in demand. For those interested in multifamily or land-flipping ventures, Riley’s journey provides both practical insights and inspiration.
Watch the Full Interview
This episode is packed with information for anyone interested in real estate investing, whether they’re new to the market or experienced investors looking to scale up. Catch the full interview with Riley Oickle on our YouTube channel or listen on Spotify or Apple Podcasts.
