What does it take to turn decades in the restaurant business into a $450 million real estate empire? In this episode, Garret Wong sits down with multifamily investor, author, and educator Gino Barbaro to unpack his incredible journey from owning an Italian restaurant in New York to building one of the largest educational communities in multifamily real estate.

Gino shares the hard lessons from losing $172,000 on his first deal, the power of mentorship, and why true wealth comes from purpose, not just money.

Timestamps:

[00:00:00] Introduction:

Garret introduces Gino Barbaro and opens with the surprising parallels between the restaurant grind and real estate investing.

[00:01:00] From Pizza Guy to Property Pro:

Gino shares his early story, growing up the son of Italian immigrants, working in his father’s restaurant, and realizing he wasn’t living his dream.

[00:05:00] The Great Reset:

How the 2008 recession forced Gino to rethink his path, discover real estate, and meet his business partner, Jake Stenziano.

[00:17:30] The $172,000 Lesson:

The painful story of Gino’s first real estate deal gone wrong—and how it shaped his investment philosophy forever.

[00:20:30] Building While Working:

Balancing a full-time restaurant business while acquiring multifamily properties one at a time.

[00:28:50] The “Jockey Framework” for Passive Investing:

Gino breaks down his 3-step model for evaluating deals and sponsors: the jockey, the saddle, and the horse.

[00:34:30] Why Coaching Collapses Time:

Both Garret and Gino discuss the difference between free advice and mentorship that actually holds you accountable.

[00:44:45] From Real Estate to Money Coaching:

Gino explains his shift from multifamily education to becoming a certified money coach—and what “Happy Money” really means.

[00:49:10] The Moment He Almost Quit:

A story about faith, frustration, and rediscovering purpose that changed Gino’s life and career direction.

[00:53:50] Defining Success:

Gino closes with his personal definition of “winning”—and the mindset that separates long-term investors from gamblers.

Key Takeaways:

• Hardship often precedes clarity—Gino’s greatest loss became the foundation of his success.
• Mentorship shortens the learning curve; experience without guidance is just expensive trial and error.
• Real wealth is about freedom and impact, not accumulation.
• Your relationship with money determines your results—learn to earn happy money.
• Purpose and family should be the true metrics of success.

About the Guest: Gino Barbaro

Gino Barbaro is an investor, entrepreneur, and author who has grown his multifamily real estate portfolio to over 2,000 units and $450 million in assets under management. A former restaurant owner for more than 20 years, Gino co-founded Jake & Gino, one of the premier multifamily education communities in the U.S. He’s a best-selling author of Wheelbarrow Profits, The Honey Bee, and Family, Food, and the Friars, and currently runs Barbaro 360, where he helps families and entrepreneurs redefine their relationship with money.

Mentioned in this Episode:

• Wheelbarrow Profits by Gino Barbaro & Jake Stenziano
• The Honey Bee by Gino Barbaro & Jake Stenziano
• Family, Food and the Friars by Gino Barbaro
• Happy Money, Happy Family, Happy Legacy by Gino Barbaro
• Rich Dad Poor Dad by Robert Kiyosaki
• Jake & Gino Community

Connect with Gino Barbaro:

🌐 Website

📘 LinkedIn

📖 Instagram