Most of us don’t realize this, but our dreams die long before we’ve even tried to make them happen. We think it happens after a failed business, a bad job, or a tough season, but it starts in childhood.

Without even noticing, we begin capping our ambitions to match our current circumstances. We play small, not because we want to, but because we’ve convinced ourselves the “big wins” are for other people.

And when those limits follow us into adulthood, the damage is exponential, especially in business and investing. We end up making decisions based on fear, not opportunity.

In this episode, I take you back to my eight-year-old self at a Monopoly board. That game shaped how I saw money and how I played for years.

I’ll share why I avoided “Boardwalk,” not just in Monopoly, but in life. And I’ll explain how changing my relationship with money completely rewired the way I play today.

Things You’ll Learn In This Episode

• The silent killer of ambition What subtle childhood messages about money and “realistic” dreams are still running the show in your financial life?
• “Boardwalk” isn’t the goal How can reframing big-ticket investments change your strategy (and your stress) forever?
• Breaking generational money habits Most parents accidentally teach their kids the wrong lessons about money. How do we create a legacy of confidence and wealth instead?
• The mindset shift that multiplies opportunity Why should we stop asking, “Can I afford this?” and start asking, “How can I make this work for me?”

About Your Host

Remington Ramsey is a speaker, author, entrepreneur, and visionary in the world of real estate. As the creator of "Real Producers", a widely acclaimed magazine connecting top agents and industry leaders, Remington has built an impressive platform dedicated to celebrating and elevating the real estate community. Remington is also the author of Agent Allies: Building Your Business With Strategic Real Estate Partnerships. With a passion for motivating and mentoring, he’s shared stages with some of the biggest names in business, helping professionals break through barriers and reach new heights. When he’s not busy being a real estate guru, Remington is known for his contagious energy, practical wisdom, and a good dose of humor—because let’s face it, navigating life and business requires both grit and a sense of humor. With multiple successful ventures under his belt and a reputation for engaging storytelling, he has the rare ability to make even the driest industry stats sound exciting.

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