Real Talk With Gary - Real Estate Investing

Real Talk With Gary - Real Estate Investing

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 2014. Gary has helped hundreds of clients with creating a wealth strategy plan through public speaking, online webinars and even has his own podcast channel dedicated to inspire and educate anyone willing to change their mindset. He continues to play an active role in his community by attending corporate, private and school events to educate adults and especially children. Gary’s inspiration and hard work comes from his passion in helping others and wanting to make a difference in their lives. “Being able to design a lifestyle of your choice is not an easy feat, however, it’s attainable as long as you have passion and know what your ‘why’ is. “ - Gary Hibbert


June 19, 2024 62 mins

Insights From a Contractor Turned Investor: RE Strategies Working Today w/Jeff Lee #263


Jeff Lee of Complete Contracting Solutions, an investor-focused renovation company, with 20+ years in the contracting industry and personal experience as a real estate investor joins me and Christopher Hummell in studio to discuss what’s working in real estate right now - student rentals, duplex conversions, ADU or garden suites, flipping etc....

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Bankruptcies On The Rise: How To Handle Your High Debts w/Wesley Cowan #262


Wesley Cowan, Senior VP, partner Licensed Insolvency Trustee at MNP joins me to talk about what’s happening out there with people overextending themselves and carrying more debt then ever before and the number of people declaring bankruptcy; mortgages becoming unaffordable; the difference between a consumer proposal and bankruptcy, and the other tools Wes...

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Staging for Success: Navigating the Entrepreneurial Journey w/Farah Singh #261


Farah Singh is a former journalist and meteorologist, and is the owner of Alt Interiors. After designing her own house, her natural design sense lead her to start her own business, which has grown to 12 staff in 8 years. Together, they’ve staged 1000’s of properties, helping sellers get anywhere from $10,000 to $200,000 extra above asking. She sees sta...

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The Transformative Power of Storytelling w/Matt Lionetti #260


Matt Lionetti, a real estate agent with Real and content creator whose funny, clever and sometimes polarizing content and unconventional approach has earned him thousands of viral views. It’s also landed him onstage alongside thought leaders like Gary Vee and Ryan Serhant. We dive into his early lack of success in real estate that had him thinking of leaving the career...

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Fighting Back Against the War on Landlords w/Weiting Bollu #259


Weiting Bollu, co-founder of began her investment journey with a very costly lesson by losing $35,000 due to a bad tenant, and while this is becoming more of a common theme, things are changing. Openroom is the platform and website she and her husband created to help others avoid certain tenants, and create a transparent rental ecosystem. We discuss exact...

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The Blueprint for Realtor Success w/Melissa Flynn #258


Public speaker and award winning real estate agent Melissa Flynn was the top agent in ONR for 2023, for the number of transactions. I dig deep to discover how she’s reached this level of success, and we talk about the mistakes that she learned from, and all the habits that help her create and elevate her success. We chat about how to build a team around you with different ski...

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Empowering Investors to Invest with Confidence w/Elizabeth Kelly #257


Elizabeth Kelly was one of the top trainers for Rich Dad Poor Dad Canada for 8 years, helping 1000’s of investors begin their real estate journey. Investing since 2005, she’s open, honest and shares all the mistakes she’s made over the years. We chat about her desire to help others by coaching; how to have 1 or more side hustles and when is the right time to le...

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Is The Housing Market Leaving The Next Generation Behind w/Todd Slater #256


Today, I’m joined by Todd Slater, broadcasting not from a studio, but from his impressive workspace. Todd, in addition to hosting a fantastic radio show on 1010 airing Sundays, is the CEO of Simple Investor, a real estate group. With over two decades of experience, Todd founded his company to streamline real estate investment, relieving investors of the h...

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ChatGPT, The Future Of Real Estate & Political Divides Pt 2 w/Sandy & Kate MacKay #255


Sandy & Kate MacKay are in the studio with me for the second part of a two-part series, where we delve into their strategies for leveraging and priming ChatGPT, navigating risks as real estate investors, assessing the potential impact of the Federal Renters’ Bill of Rights, making market predictions, and much more! If you're starting small with...

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Starting Small, Building Big: The Journey w/Sandy & Kate MacKay #254


Sandy & Kate MacKay join me in studio for part 1 of a 2 part series to discuss our humble beginnings, they were only able to wholesale as they had $0, and I was trying to figure out our investment club, and we made a ton of mistakes. They have a large portfolio, plus Sandy is a realtor and operating partner at Keller Williams. They also have a property managemen...

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Scaling Your Business: From Chaos To Order w/Adriana Ostapenko #253


Adriana Ostapenko is living proof that you can start with little and build your own empire. We dive in to how she’s built her empire in the multi-family space; the ‘purchase plus’ improvement strategy; The MLI Select CMHC product that she’s taken advantage of; Where’s she’s investing; HOW to scale successfully, plus MUCH MORE! If you are curious about U.S. Invest...

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U.S. Real Estate Investing For Canadians: A Gateway To Growth w/Nate Atkins & Neil D’Souza #252


Nate Akins is a successful 20-year asset and property manager, and Neil D’Souza is a successful mortgage broker, and parter with Gary in Deep Pockets. We discuss a new partner venture with us plus Thomas Lorini about getting started in investing in real estate in the US. Why now, why the US and more specifically why Cleveland Ohio? We ...

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How Can Spouses Successfully Build a Business Together w/ Lena Guirguis #250


Lena Guirguis is an investor since the age of 21, asset management specialist, mom, wife and has co-founded many successful ventures. How DOES she do it all, and how HAS she done it all? She works with husband, so we look at what it takes to make it work; how opposites attract and how that is GREAT for working with your spouse; what is Stilettos and Hamm...

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Mistakes Made in a HOT Market w/ Dave Butler #249


Dave Butler who is an entrepreneur, mortgage agent and good friend joins me in studio to discuss everything mortgage - what’s happening in the market; what are some of the new programs to help homebuyers and investors; 1st & 2nd mortgages and promissory notes in the news; how to protect yourself; understanding loan to value; the dangers of being over-leveraged; are interest rate c...

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Power Of Sale; Closing Disputes & Using VTBs w/Allison McMurter #248


Allison McMurter, part of the trusted legal team of McMurter & Associates joins me and Quinton Cordick in studio to get the down low on Foreclosures & power of sale how they are different; Are appraisals coming in at what’s needed these days; What else is going on in the market; Different disputes on closing or after; Permit searches before closing; Financing an...

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#247: Denise & Nicolee - Strategies for Self-Employed Canadians: Making the Most of Your Mortgage


Denise Laframboise & Nicolee Evans are experienced mortgage agents from, and join me in studio to talk mortgages, especially as a self employed person and why they have difficulty getting qualified; rates; why rates are not always what to focus on; starter homes; house hacking; creative financing and MUCH MORE!...

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#246: Jeff Ortiz - From Colombia to Building a Multi-Family Legacy


Jeff Ortiz from Ortiz Equity Group joins me in studio to talk about building and leaving a multi-family legacy! Jeff and his brother John started off with wholesaling, but now typically invests in multi family homes in South and North Carolina, and also Georgia. He walks us through the process of finding B and C class homes, homes that have some room for improveme...

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#245: Michael Lombardi - House Hacking for Real Estate Wealth: A Path To Success


Michael Lombardi was a house hacker before he’d ever heard the term! He realized that by buying a property with rental income, it would cost him less to carry the property than if he’d bought a cheaper property and was the only resident. His journey began in 2016 in Toronto, purchasing a house and adding 3 units to it. He currently owns 7 properties,...

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#244: Joel Friedland - Raising Money, Going Debt-Free & How to Survive A Mental Crash

I hopped on Zoom with investor Joel Friedland, with a 42 year track record of over 2000 industrial leases and over $2 Billion in brokerage volume! He also does syndicated deals with 0 debt which is unheard of approach. We dive in to how he does that, WHY he does that, and how he raises capital for these deals; the 2008 crash and how it lead to a d...

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#243: Jacob Asparian - Could Bitcoin Replace Traditional Currencies in the Future?


I sit down with Jacob Asparian, real estate investor, broker and also founder and CEO of, a platform created to help Canadians access Bitcoin in a safe and convenient manner. He joins Christopher Hummell and myself to discuss what is known about Bitcoin and what is myth, how it differs from cryptocurrency; is Bitcoin an currency or an a...

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