We often view “legacy” as a static number left behind in a trust fund. But for Gino Barbaro—entrepreneur, real estate titan, and author of Happy Money Happy Family Happy Legacy—legacy isn’t just what you leave for your family; it’s how you live with them.
In a recent “Expert Inside Interview,” Barbaro shared his evolution from a stressed-out restaurant owner to managing over $450 million in real estate assets. His journey offers a masterclass in shifting from working for money to making money work for your happiness.
From “Buying a Job” to Building Wealth
Gino’s story began in the restaurant industry, following in his father’s footsteps. However, he quickly realized he hadn’t bought a business; he had purchased a job. He was trading time for dollars, a cycle that offered no true freedom. The pivot came when he embraced real estate, starting with a modest fourplex.
His advice? Start small, but start now. You don’t need a home run on your first swing. You need to get on the field, make mistakes, and build resilience.
The Philosophy of “Happy Money”
One of Barbaro’s most transformative concepts is the distinction between “Happy Money” and “Unhappy Money.”
- Unhappy Money is earned through stress, ethical conflict, or work that drains your spirit. It feels heavy and creates anxiety.
- Happy Money is the result of aligning your income with your values and passion. It brings energy, freedom, and a sense of lightness to your household.
The goal isn’t just to increase your net worth; it is to improve the percentage of “Happy Money” flowing into your life.
Bringing the Family to the Boardroom
Perhaps the most disruptive idea Barbaro advocates is treating the family unit like a business. Most families operate on autopilot; Barbaro suggests operating on purpose.
He recommends creating a Family Mission Statement and holding weekly family meetings. But he goes a step further: he invites his children to monthly calls with his bookkeeper. By normalizing conversations about assets, liabilities, and cash flow, he removes the taboo and shame often associated with money. This prepares children for the real world by teaching financial literacy through real-life observation rather than textbook theory.
The Power of “Skin in the Game”
Finally, Barbaro attributes his acceleration to self-education and mentorship. But he warns against the trap of free advice. He emphasizes that paying for mentorship creates “skin in the game.” When you are financially committed to your own growth, your accountability skyrockets.
3 Steps to Build Your Legacy Today
If you want to replicate this level of fulfillment, start here:
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- Audit Your Income: Is your money “Happy” or “Unhappy”? If it’s the latter, map out an exit strategy.
- Open the Books: Stop hiding money struggles or wins from your kids. Age-appropriate transparency builds trust and intelligence.
- Define Your Values: Sit down this week and write out what your family stands for. Make it your North Star.
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