The Wealth Game: Are You Playing Checkers or Chess?
There was a moment during my conversation with Freddie Rappina that completely reframed the way I think about wealth building.
He said most people are playing checkers while the wealthy are playing chess.
And honestly, that analogy stuck with me long after the episode ended.
Because the truth is, so many professionals, especially real estate agents, spend their lives helping other people build wealth while neglecting to build their own.
As Freddie pointed out, many agents are incredible at helping clients buy investment properties, grow equity, and create financial opportunity, yet they often fail to pause and ask themselves:
What am I building for my own future?
The Shoemaker With No Shoes
Freddie called it the “shoemaker with no shoes” problem.
And if we’re being honest, this happens everywhere, not just in real estate.
We get so busy producing, serving, solving problems, and surviving the day to day demands of life that we never step back to intentionally design wealth.
Not income.
Not commission checks.
Not survival.
Wealth.
And according to Freddie, the difference comes down to understanding which game you’re playing.
Checkers vs. Chess
The “checkers” model is the traditional financial advice most people grow up hearing:
• Save as much as possible
• Fully fund retirement accounts
• Pay off all debt
• Build emergency savings
• Delay gratification for someday later
And to be clear, there’s nothing inherently wrong with that.
Freddie makes an important distinction throughout the conversation: you can live a happy, stable life playing checkers.
But chess is different.
Chess focuses on:
• Building income streams
• Acquiring cash flowing assets
• Using leverage strategically
• Creating wealth that works for you now and in the future
That’s the shift.
Not just saving money, but creating systems that generate money.
The Mindset Shift Most People Never Make
One of the most important points Freddie made was that the first chess move isn’t buying real estate.
It’s mindset.
Because before anyone can build wealth differently, they have to think differently.
And nowhere is that more evident than in the conversation around debt.
In the “checkers” mindset, debt is the enemy. The goal is eliminating it entirely.
In the “chess” mindset, debt becomes a tool.
Not reckless debt.
Not overleveraging.
Strategic debt.
The type used to acquire assets that generate income and eventually pay for themselves.
That’s a completely different way of viewing money.
Why Cash Flow Matters More Than Hype
One of my favorite parts of the conversation was Freddie’s perspective on real estate investing in today’s market.
While so many people obsess over appreciation and timing the market, Freddie kept bringing the conversation back to one thing:
Cash flow.
Because appreciation is hypothetical until you sell or refinance.
Cash flow changes your life now.
Cash flow pays for:
• Your kids’ activities
• Your travel
• Your flexibility
• Your freedom
• Your ability to stop trading every hour for dollars
That perspective feels especially relevant in today’s market where fear, headlines, and noise dominate so many conversations.
Freddie’s approach was refreshingly simple: buy assets that produce income regardless of whether the market is up, down, or sideways.
The Financial Lesson Schools Still Aren’t Teaching
There was also a moment in the episode that honestly made me laugh and then immediately made me think.
Freddie shared that his son recently took a high school personal finance course and described it this way:
“Dad, it’s teaching people how to live broke instead of how to become rich.”
And while that statement may sound blunt, it highlights a much bigger issue.
We teach people how to budget.
How to survive.
How to avoid mistakes.
But we rarely teach:
• How to create value
• How to multiply value
• How wealth is actually built
Freddie simplified it beautifully:
• Produce value
• Store value
• Multiply value
That’s the real wealth conversation.
You Don’t Have to Play on Elon Musk’s Level
Another point that really resonated with me was Freddie’s reminder that you do not need to operate on billionaire scale to think differently.
You don’t need:
• Private jets
• Hedge funds
• Massive corporations
You simply need awareness.
Awareness that there are different strategies available.
Different ways to structure wealth.
Different ways to use money.
And perhaps most importantly, the willingness to learn a different game.
Final Thoughts
This conversation wasn’t really about checkers or chess.
It was about intentionality.
About understanding that wealth rarely happens accidentally.
And about realizing that many of the systems wealthy people use are not hidden, they’re simply viewed differently.
The question is:
Which game are you playing?
And even more importantly, is it the game you actually want to be playing?
If this conversation sparked a shift in your thinking, I highly recommend checking out Freddie Rappina’s book, Playing the Wealth Game, and listening to the full episode of Pending & Trending.
