Jack Bernstein is a serial entrepreneur and established real
estate investor with an impressive journey rich with experiences to
share. As a child growing up in Mississauga, he was surrounded the
better things in life, sparking curiosity about a life beyond his
own. After a short career as a professional snowboarder, he
launched a startup at the age of 18. For five years, he navigated
the stormy seas of business, learning and growing with each
However, it wasn't until a stint in tech sales that Jack discovered
the allure of real estate. He noticed his coworkers, despite
earning hefty paychecks, lived humble lives, with the bulk of their
money flowing into real estate investments. This revelation was a
turning point for Jack, leading him to purchase his first duplex in
Oakville in 2017. Today, he has built a substantial portfolio with
properties worth over $12 million. His innovative approach to real
estate can be a useful learning curve for all aspiring
In this episode, we discuss the following:
- Understanding the vital role of mentorship and guidance in a
journey to success.
- Effective real estate investing strategies from the lessons
- Scaling from residential to commercial real estate through
strategic partnerships with experts.
- Impact of interest rates and market conditions in real estate
and how to act prudently.
- Evolving future of homeownership and transition trends in the
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