From Dropout to Real Estate Mentor: How Giancarlo Built Wealth Through Property Management & Coaching

Think you need a degree to succeed in real estate? Think again.

Giancarlo Carangelo dropped out of high school at 16 and started working in restaurants—but he knew he wanted more. Tired of long hours and low pay, he took a chance on a real estate course, and that single decision changed everything.

Today, he’s a successful real estate investor, property manager, and coach.

Giancarlo didn’t grow up with a roadmap to wealth. He built it brick by brick—learning to manage properties, mentor new investors, and build a community that grows wealth together.

In this episode, you’ll discover the mindset and strategies he used to create lasting freedom—plus how you can start even if you have zero experience.

Key Takeaways:

• Why your investor personality (hands-on vs. hands-off) shapes your strategy

• How Giancarlo turned $500 into a thriving real estate portfolio

• The biggest myth about doing it all yourself—and why collaboration wins

• What it really takes to go full-time in real estate (3–5 year roadmap)

• How to shift from a worker’s mindset to an investor’s mindset

• The power of mentorship and community in long-term real estate success

About the Guest:

Giancarlo Carangelo — a seasoned real estate investor, entrepreneur, and coach who has built a powerhouse business from the ground up. With nearly $50 million in assets under management and over 300 real estate transactions completed, Giancarlo is a leading voice in the world of real estate investment and property management. He’s the founder of Carangelo Management, A Real Estate company, and ProVenture, Full service Estate firm that helps new and experienced investors launch and grow profitable portfolios across Canada, the U.S., and even internationally in markets like the Dominican Republic.

What makes Giancarlo’s journey even more inspiring is that he’s achieved all of this after dropping out of high school. Through grit, consistency, and smart strategy, he’s built a reputation as a results-driven leader who knows how to navigate complex markets, build strong systems, and scale efficiently.

Whether it’s coaching clients, speaking to an audience, or running his own podcast, Giancarlo is passionate about sharing what he’s learned and empowering others to take control of their financial future through real estate. If you're looking to get tactical insight, real-world experience, and a dose of entrepreneurial fire.

Links:

https://www.realproventure.com/

Fast Five Questions:

1. If you woke up and your business was gone, you have $500, a laptop, a place to live, and food, what would you do first? “I’m going to take all that knowledge I’ve absorbed in the last 10 years and implement a new strategy… something short-term to build capital, then transition back to long-term scalable investments.”

2. What is the biggest mistake that you have made in business? “Having the lone wolf mindset… thinking I could do it by myself without coaching or mentoring.”

3. What is a book that you would recommend? “Money People Deal by Stefan Aarnio

4. What is a tool that you use every day that you would recommend? “My cell phone. It connects me to every CRM and platform I use to run my business—anywhere in the world.”

5. What is your definition of freedom? “Being able to do what I want, when I want, with whom I want—without asking permission. Time with my family, being there for breakfast or a soccer game… that’s real freedom.”

About Jeff:

Jeff spent the early part of his career working for others. Jeff had started 5 businesses that failed before he had his first...