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How Monopoly Taught Me the Business Mistakes That Keep Entrepreneurs From Building Real Wealth

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How Monopoly Taught Me the Business Mistakes That Keep Entrepreneurs From Building Real Wealth

The strategy that wins at Monopoly quietly drains businesses, but the one that helped me beat my brother can build lasting wealth.

You never forget your first big win in business. Mine came in the form of my first victory over my older brother in Monopoly. The game turned 90 last year, and it remains one of the greatest, most ubiquitous and supremely frustrating games of all time. For nearly a century, Monopoly has taught all of us ages 8 and up how to think about money.

Buy properties. Collect rent. Build houses. Accumulate wealth. Bankrupt your competitors. It’s one of the most successful board games ever created because its rules are simple and its objective is clear: Own the most, and you win. The problem is that many entrepreneurs carry those same rules into business.

Real business doesn’t reward the person who acquires the most assets. It rewards the leader who consistently makes better decisions. Success isn’t determined by a single big move. It’s shaped by thousands of small decisions that compound over time. Ironically, Monopoly hints at this from the start. Every player rolls the same dice, and no one controls the outcome. What separates players isn’t the roll. It’s what they do next.

Business works the same way. Markets shift. Customers leave. New competitors emerge. Economic conditions change. You don’t control those events, but you do control your response. After working with thousands of business owners , I’ve found that the entrepreneurs who consistently outperform their peers share three habits.


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