
Jack Daniel Bernstein
From Snowboarder to
Serial Entrepreneur
and Real Estate Mentor
Jack’s Experience
Properties In:
Barrie, Hamilton, Oakville, Mississauga, Brantford, Owen Sound, and Blue Mountain
Portfolio
$12m+ Under Management
50M+ in real estate transacted
Serial Entrepreneur
Seriel entrpreneuer – 6X business founder
Students
100+ Students Trained 1:1
Jack Daniel Bernstein built a real estate portfolio valued at over $12M.
Watch the video below to learn more about Jack

Jack meeting Daniel Drimmer, CEO of Starlight Investments, 75,000 unit rental portfolio and 28 Billion under management
Jack started his portfolio without any help, joint venture partnerships, or assistance. He relied solely on his strategic investments and entrepreneurial grit to get where he is today.
Jack’s journey began in the corporate world, where he worked tirelessly, but in 2021, he retired to pursue real estate full-time. Starting at just 18, Jack sold his first business at 24 and transitioned into real estate, where he quickly scaled his portfolio using creative financing strategies and personalized investment techniques.
His success didn’t come from shortcuts—it came from hands-on experience and the knowledge gained from building and managing a real estate empire. Jack’s success is built on hands-on experience and the guidance of a network of highly successful mentors who have helped him gain the knowledge he applies today. These mentors offer advisory support across various industries, shaping his strategies and approach. Jack, in turn, shares these insights with his students, empowering them to succeed in real estate.
Jack’s expertise focuses on time compression—what might take years to learn on your own, you can master in a fraction of the time through his mentorship. His programs are designed to help you build wealth, achieve financial freedom, and craft the life you want through real estate investing.
If you’re ready to accelerate your journey and take control of your financial future, Jack’s coaching programs offer the support, accountability, and exclusive network to help you do so.
Real Estate has allowed Jack to travel to
50+ countries while maintaining his portfolio.






Jack went viral in 2021 with his Toronto Life article on building his story from scratch. Rags to riches.
Explore Jack’s insights and strategies with hours of free, actionable real estate content.

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