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


#180: Jack Drinkwalter - 23 Years Old 23 Doors

#180: Jack Drinkwalter - 23 Years Old & 23 Doors

On this episode Gary chats with relatively new investor Jack Drinkwalter. Jack has been investing only 4 years in North Bay, but has achieved massive success by showing no fear and knowing his numbers. He didn’t want to work a 9-5 anymore, so bought his first JV at 19 and hasn’t looked back, by refi-ing and buying multi-unit. No matter your age, if YOU are wanting more time and money freedom than a 9-5 job offer you, THIS podcast is for you!



  • How his first property ignited his property acquisitions
  • Who was his first JV partner
  • Does his still believe in JVs
  • Why he only owns ONE single family home - his own
  • Why multi family
  • Why he believes investors, and ordinary people should show no fear and pursue their dreams
  • Is he stopping at 23 doors
  • How he moved from a car salesman in the pandemic to a full time investor
  • Why he now owns a property management company serving other investors
  • Tenants
  • And MORE!



Hi, I’m Jack Drinkwalter, I’m a young real-estate entrepreneur born and raised in North Bay, Ontario. I started buying rental properties while attending my local University and working full time as a car salesman. My first deal was a house Hack. I purchased a 5-bedroom house, lived in one bedroom and rented out the others to friends. In 2020 during covid I purchased my second property with a JV partner (My Dad) we purchased a run-down duplex and implemented the BRRRR strategy. After refinancing my second deal I’ve been able to scale fairly quickly. I now own 8 properties (23 units) and a property management/contracting company “Aedo Properties” that currently manages 40 units for other investors. 

Contact Jack: 

Insta: jack_therealestateinvestor


This episode proudly sponsored by Brian Daley @ AGHI Home Inspections.

Whether buying or selling a property, AGHI recognizes that the process can be stressful. It is critical that any decision you make be one that is based on knowing all of the facts. Purchasers, vendors, insurance companies and lending institutions have come to recognize the professionally trained residential home inspector as a credible source of key information vital to making these decisions, and AGHI has been doing it for over 15 years!


Contact  or call (416) 526-7482


Other Links:

Private Investing, visit

Real Estate Investment Club visit 

Gary's mentorship program visit 

Start your own Podcast visit 



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