Cover art for podcast Real Talk With Gary - Real Estate Investing

Real Talk With Gary - Real Estate Investing

168 EpisodesProduced by Gary Hibbert Real Estate InvestorWebsite

Gary Hibbert is a Full Time Real Estate Investor, Licenced Real Estate Agent, achieving various Realtor awards and an Educator. In 2008, he purchased his first investment property and through hard work and dedication, left the regiment of the corporate world to become a Full Time Entrepreneur in 201… read more


#133: Josh Stevenson - The Millionaire Schoolteacher, From The Classroom To RE Wealth

#133: Josh Stevenson - The Millionaire Schoolteacher, From The Classroom To RE Wealth

On this week’s show Gary chats with former ESL and regular teacher Josh Stevenson from While he began as a teacher, both overseas and in Canada, his grandparents, not his parents were entrepreneurs, owning hotels and various properties. His parents were also teachers and loved the steady income, but Josh wanted more, so after going bankrupt, decided he needed to reinvent himself, and did he ever! He now owns over 80 doors worth $18 Million+ and is not stopping! Take notes, you’ll learn quite a few things in this action-packed podcast!


  • Why you should NOT be afraid of owning property at a distance
  • How you can hack property management
  • How he scaled his business with a partner
  • How the cash flow from his properties allowed him quit teaching and ‘retire’, and allow he and his partner to live comfortably
  • How he cashed in his pension to buy property (WHAAAAAT?!)
  • Why he loves multi family units
  • Why he hasn’t done ANY Joint Ventures
  • VTBs - Vendor Take Backs
  • Why financial literacy should be taught in school
  • And MORE!


Josh’s Bio

Josh Stevenson is the co-owner of a property investment company called Invest North which holds 87 doors valued at over $14M in Orillia, Severn Township, Sundridge, Rutherglen, North Bay, Cobalt and New Liskeard. Josh retired from his grade 8 teaching job in November of 2020 after a 20-year career that took him to Japan, The Czech Republic, Taiwan, Australia and finally back to Ontario.

He and his business partner, Brent Peterson, manage all 87 doors with the help of their wives and they have managed to build their portfolio with absolutely no joint venture partners. Josh regularly works with credit unions to buy buildings with a “no-money-down strategy”. His use of creative financing techniques and vendor take-back mortgages has allowed Invest North to add over 60 doors during the past two years he and his partner plan to continue their expansion into Ontario’s northern markets for the foreseeable future.

Josh is married to the author Jessica Hamilton and they live with their two children in Orillia, Ontario.

Website/contact info for guest



This episode proudly sponsored by Property Pathways -

Property Pathways is an investor-focused architectural design service provider that specializes in secondary suite conversions throughout Ontario. We'll assist in developing a strategic design and renovation plan that will get the most out of your investment property.

Interested in learning more about Real Estate Investing? Visit

Real Estate Investment Club visit

Gary's mentorship program visit

Start your own Podcast visit-


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